JP2015151339A - 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol and process for producing the same - Google Patents

Abstract

【Task】
An object of the present invention is to provide novel bisphenols that are useful as raw materials for phenol resins, epoxy resins, epoxy resin curing agents, polycarbonates, polyesters, urethane resins, and the like, which can be derived from lignin.
[Solution]
An object of the present invention is to provide 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol and 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol, and an acid. 3,3-bis (4-hydroxy-3-methoxyphenyl) -1 comprising the step of obtaining 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol by contacting with a catalyst -Solved by the production method of propanol.
[Selection figure] None

Description

The present invention relates to 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol, which is a novel bisphenol, and a method for producing the same.

Bisphenols having two or more hydroxyphenyl groups are a variety of novel polymers, such as epoxy resins, polycarbonate resins, and acrylate resins, utilizing the reactivity of the hydroxy groups bonded to the aromatic rings in the molecule and the aromatic rings themselves. It is widely used as a starting material for polyurethane, aryl oligomers and the like. Such bisphenol-derived resins are applied to various uses such as optical materials and electronic materials. Thus, bisphenols are attracting particular attention because they have a variety of reactions and are versatile enough to enable a wide variety of applications.

As bisphenols, for example, Non-Patent Document 1 describes that having a hydroxypropyl group between two hydroxyphenyl groups, 1- (4-hydroxy-3-methoxyphenyl) -1, 3- (hydroxyphenyl) -3- (4-hydroxy-3-methoxyphenyl) -1-propanol and 3,3-bis (hydroxyphenyl) obtained by reacting 3-propanediol with 10 times the weight of phenol -1-propanol is disclosed.

Von K. Kratzl: Holzforschung (1980), 34, 191-196

Certainly, Non-Patent Document 1 discloses 3- (hydroxyphenyl) -3- (4-hydroxy-3-methoxyphenyl) -1- as bisphenols having a hydroxypropyl group between two hydroxyphenyl groups. Propanol and 3,3-bis (hydroxyphenyl) -1-propanol are disclosed. However, the substitution position of the hydroxy group in one aromatic ring is unknown, and only a mass spectrum is shown as a structural analysis. Therefore, the structure disclosed in Non-Patent Document 1 is not well-founded, and bisphenols having a hydroxypropyl group between two hydroxyphenyl groups are disclosed in such a manner that they can be actually produced and used. I can't say.

In addition, the present inventors proceeded with research on an effective utilization method of lignin, and used 3-hydroxy-1- (4-hydroxy-3-methoxyphenyl) -1-propanone as a degradation product of lignin by microbial treatment. Attention has been focused on 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol obtained through the process.

However, since the diol compounds are not the same in reactivity as the bisphenols, it is difficult to obtain a polymer having a certain repeating unit such as gelation even when subjected to a polyester or polyurethane synthesis reaction. . Moreover, in order to exhibit the performance as an adhesive or a resin product for molding, problems remain with respect to compatibility and reactivity with the resin used together.

Therefore, the present invention is derived from 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol and 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol. The problem to be solved by the invention is to provide a highly practical compound as compared with the above.

As a result of intensive studies to solve the above-mentioned problems, the present inventors contacted 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol with an acid catalyst. As a propanol compound having 4-hydroxy-3-methoxyphenyl groups, 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol was successfully obtained. The present invention is a completed invention based on such a successful example.

Therefore, according to the present invention, 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol is provided.

According to another aspect of the present invention, 3,3-bis (4-hydroxy-) is obtained by contacting 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol with an acid catalyst. A method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol is provided, which comprises the step of obtaining 3-methoxyphenyl) -1-propanol.

Preferably, in the production method of the present invention, the acid catalyst is hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, potassium monosulfate, sodium monosulfate, potassium monophosphate, formic acid, acetic acid. And an acid catalyst selected from the group consisting of oxalic acid.

According to the present invention, compared to 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol, 3,3-bis (3), which is a novel bisphenol suitable for polymer synthesis, 4-hydroxy-3-methoxyphenyl) -1-propanol is provided. The 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol of the present invention is soluble in an organic solvent, and further used as a plastic raw material such as an epoxy resin or a resin additive. A wide range of compounds.

According to the production method of the present invention, such industrially useful 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol can be produced.

Details of the present invention will be described below.
The present invention relates to 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol, which is a novel bisphenol compound. 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol is a compound having a structure represented by the following formula (III) and a molecular weight of 304.
(III)

The 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol of the present invention can be used as a raw material for phenol resins, epoxy resins, epoxy resin curing agents, polycarbonates, polyesters, urethane resins and the like. For example, specifically, it can be used as a curing agent for epoxy resins, such as 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol and 2,2-bis (4-glycidyloxyphenyl). A cured epoxy resin is obtained by mixing and curing an epoxy resin such as propane and a curing accelerator.

In addition, 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol of the present invention can be prepared by, for example, adding an epichlorohydrin to a hydroxy group bonded to a phenyl group in the molecule, and It can be epoxidized according to a conventional method such as ring closure using Examples of such a compound include compounds represented by the following formula (IV).
(IV)

The 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol of the present invention can be produced, for example, by the production method of the present invention described later.

The method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol of the present invention comprises 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol, an acid catalyst To obtain 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol.

In the production method of the present invention, 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol represented by the following formula (II) known so far is used as a raw material.
(II)

The method for obtaining 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol is not particularly limited. For example, as described in Non-Patent Document 1, 4-benzyloxy-3-methoxy It can be produced and obtained by a method of synthesis from benzoyl acetate ester in several steps including a reduction reaction using lithium aluminum hydride. As another example, as shown below, the present inventors have invented 3-hydroxy-1- (4-hydroxy-3-methoxyphenyl) -1-propanone represented by the following formula (I): Can be obtained and obtained by a method for producing 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol.
(I)

That is, 3-hydroxy-1- (4-hydroxy-3-methoxyphenyl) -1-propanone is added to a mixed solution of water and an aqueous sodium hydroxide solution and stirred at 10 to 45 ° C. A solution containing -1- (4-hydroxy-3-methoxyphenyl) -1-propanone is obtained. While stirring the resulting 3-hydroxy-1- (4-hydroxy-3-methoxyphenyl) -1-propanone-containing solution, sodium borohydride was added in small portions at several minutes to several hours at 10 to 45 ° C. Add. The solution to which sodium borohydride has been added is allowed to react with stirring at 10-45 ° C. for several hours. After confirming disappearance of 3-hydroxy-1- (4-hydroxy-3-methoxyphenyl) -1-propanone, an aqueous hydrochloric acid solution was gradually added dropwise to the solution after the reaction to adjust the pH to 3.0-10. Then, an organic solvent that is incompatible with water is added, and 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol is extracted and separated. The aqueous layer is re-extracted using the organic solvent. This is repeated one to several times. The obtained extracts (organic layers) are combined, washed with an aqueous solution containing a weak base, and further washed with water. From the washed extract, the organic solvent is distilled off under reduced pressure or at a low temperature to obtain 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol.

Although there are no particular limitations on the means and conditions for the reaction of producing 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol and an acid catalyst to produce the desired product, water, alcohols, ketones It is preferable to carry out the reaction in the presence of a solvent such as an alcohol, an ether, an aprotic polar solvent, a halogenated carbon, or an aromatic compound. When only water is used as a solvent, the target product tends to be separated into an oily or resinous form as the target product is formed, causing problems such as adhesion to the reactor. there is a possibility. Therefore, in order to avoid this problem, it is possible to use a mixed solvent in which water and an organic solvent are used in combination.

Specific organic solvents include alcohols such as methanol, ethanol, isopropanol and butanol; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; ethers such as THF, dioxane and diglyme; aprotic Examples of polar solvents include dimethylformamide, dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, etc .; examples of halogenated hydrocarbons include chloroform, methylene chloride, dichloroethane; and examples of aromatic compounds include benzene, toluene, xylene, chlorobenzene, and the like. Although each is mentioned, it is not limited to these.

When using an organic solvent, depending on the reaction conditions, a by-product in which the benzylic position of the target product is alkoxylated when using alcohols, or a by-product in which the target product is ketalized is generated when using ketones. there's a possibility that. In order to avoid this, it is preferable to coexist water of about 0.1% V / V or more.

The amount of solvent used can be appropriately set according to the type of solvent and the amount of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol used, and is not particularly limited. The amount is about 1 to 100 times by weight, preferably 3 to 50 times by weight with respect to (4-hydroxy-3-methoxyphenyl) -1,3-propanediol.

The acid catalyst is not particularly limited as long as it is an acidic substance that is known to be used as a normal catalyst. For example, strong acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid; And weak acids such as sodium monosulfate, monobasic potassium phosphate, formic acid, acetic acid and oxalic acid; and Lewis acid catalysts such as boron trifluoride-ether complex and lanthanoid triflate. The amount of the acid catalyst used can be appropriately set according to the amount of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol used, and is not particularly limited. The amount is 0.01 to 20 times mol, preferably 0.05 to 5 times mol, based on (hydroxy-3-methoxyphenyl) -1,3-propanediol.

Contact of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol with an acid catalyst is carried out by using 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol and An embodiment in which an acid catalyst is added and contacted, an embodiment in which 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol is dissolved or dispersed in a solvent and then contacted by adding an acid catalyst, in a solvent A mode in which 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol is added and brought into contact after the acid catalyst is dissolved or dispersed is conceivable. Is a mode in which 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol is dissolved or dispersed in a solvent and then contacted by adding an acid catalyst. In the contact, it is preferable to stir the mixture containing 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol and the acid catalyst. Therefore, the contact is performed by dissolving or dispersing 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol in a solvent, adding an acid catalyst while stirring, and heating as necessary. Is more preferable.

The reaction temperature is not particularly limited as long as it is a temperature at which 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol and the acid catalyst are in contact with each other, and is, for example, 30 to 150 ° C., preferably 50-90 ° C. The reaction time is not particularly limited as long as it is confirmed that the target product 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol is sufficiently produced. -50 hours, preferably 2-30 hours. Since the reaction time is related to the reaction temperature with respect to the production amount of the target product, it is more preferable to set the reaction time by tracking the progress of the reaction by HPLC or the like.

3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol can be identified as a peak with a retention time of 7.9 minutes, for example, by HPLC measurement under the conditions described in Example 1 described below. The quantification can be performed by using a commonly known quantification method such as a calibration curve method or an internal standard method. Moreover, 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol can be identified as a peak at a retention time of 4.3 minutes by HPLC measurement under the conditions described in Example 1 described later.

The presence of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol as a raw material was sufficiently reduced by HPLC or the like, and 3,3-bis (4-hydroxy- By confirming that a sufficient amount of 3-methoxyphenyl) -1-propanol has been produced, the reaction end point can be determined. The target 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol can be directly recovered from the reaction solution after completion of the reaction. For example, the reaction solution can be treated as follows. It is preferable to provide.

The reaction solution is neutralized by adding an alkali corresponding to the amount of the acid catalyst used to stop the reaction, and then the solvent used is distilled off to recover the target product. The alkali used here is not particularly limited as long as it is an alkali used in general neutralization applications. For example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, acetic acid. Sodium, potassium acetate, triethylamine, pyridine and the like can be mentioned.

In removing the catalyst residue from 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol, the solvent was distilled off, water was added, and the water was non-phasic. It can be removed by adding a soluble organic solvent, extracting the target product into the organic layer, and transferring the catalyst residue to the aqueous layer. Of course, when contacting 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol with an acid catalyst, water, a mixed solvent containing water, and a two-phase solvent composed of water and an organic solvent are used. Then, 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol which is the target product can be easily recovered after the reaction.

The amount of the solvent used for extraction of the target product is affected by the solubility of the target product, and can be, for example, about 2 to 100 times the weight of the target product. Moreover, the temperature and the frequency | count at the time of extraction are not specifically limited, For example, temperature is made into room temperature vicinity and the frequency | count of extraction can be 1 to several times, Preferably it can be set to about 1 to 4 times.

In order to obtain the target product at a high concentration, the solvent is preferably distilled off from the obtained extract by means such as distillation or azeotropic distillation. The solvent is preferably distilled off under reduced pressure or at a low temperature. In this way, the desired 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol is obtained in a semi-solid state and tends to solidify in the cooled state.

3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol can be used as a crude product depending on the purpose and purpose of the epoxy resin, its curing agent, phenol resin and the like. However, since the crude product contains a polymer substance, it is preferably used as a refined product by subjecting it to purification means such as column treatment, recrystallization, and reprecipitation, depending on the application and purpose. As a specific example of the purification of 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol, the method described in Example 3 described later can be given.

In the production method of the present invention, as long as the object of the present invention can be achieved, various processes and operations can be added before or after the above-described process.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples, and the present invention can take various modes as long as the problems of the present invention can be solved. .

[Example 1. Method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol using methanesulfonic acid as an acid catalyst]
To a 50 ml round bottom flask, 15 ml of water and 0.4 g of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol were added and dissolved at room temperature with stirring. To this round bottom flask, 44 mg of methanesulfonic acid was added and reacted at 65 ° C. for 22.5 hours.

An oily substance was separated in the round bottom flask after completion of the reaction. To this round bottom flask, 0.46 g of 1N sodium hydroxide aqueous solution was added to neutralize the acid catalyst methanesulfonic acid.

Ethyl acetate was added to the neutralized solution at room temperature, and the mixture was stirred and the ethyl acetate layer was separated to extract the desired product. Extraction was performed twice using 10 ml and 5 ml of ethyl acetate, respectively. When ethyl acetate was distilled off from the obtained extract, 0.32 g of a viscous liquid was obtained. The purity of this product as 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol was measured under the following conditions, and it was 68% as an area percentage without sensitivity correction. It was.

HPLC conditions:
Apparatus: Waters 2795, 2998
Column: X-bridge C18, 3.5μ, diameter 4.6 mm × 100 mm, (30 ° C.)
Carrier: (A) 2 mM NH ₄ OAc aq. (0.05% V / V Formula acid) (B) MeOH
Gradient: MeOH 5% V / V (1 min), MeOH 5% V / V → 95% V / V (1-15 min), 95% V / V (15-18 min)
Detector: UV270nm

Similarly to the method described in Example 3, the obtained liquid was dissolved in a mixed solvent of ethyl acetate: toluene = 1: 1, applied to a silica gel column (Wakogel C-200), and ethyl acetate: toluene = 2: 3. A purified product was obtained by concentrating the main product fraction obtained using a developing solvent.

This purified product was subjected to reversed-phase UPLC-time-of-flight accurate mass spectrometry (ACCUITY UPLC H-Class, XevoG2 QTOF; manufactured by Waters) under the following conditions, and when the mass spectrum was measured, a negative ion of 303.123 was detected. did. This corresponded to a mass of molecular weight −1 of 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol.

Reverse phase UPLC condition column; ACQUITY UPLC HSS T3 C18 Column, 1.8 μm, 2.1 mm × 100 mm (manufactured by Waters),
Eluent: (A) [2 mM ammonium acetate, 0.05% V / V formic acid], (B) methanol,
Liquid feeding: 0-5 minutes 5% V / V-95% V / V (B); 5-7 minutes 95% V / V (B),
Column temperature: 40 ° C., flow rate: 0.4 ml / min

Mass analysis condition detection mass range 100-1000 Da, data acquisition scan interval 0.1 second, desolvation gas temperature 500 ° C., ion source ESI negative mode ion source temperature 150 ° C., cone voltage 20V

Next, the results and attribution of NMR spectra measured using a 400 MHz nuclear magnetic resonance absorber are shown. These analytical results support the structure of 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol.

1H-NMR (CDCl3 solvent)
2.23 ppm; ddd, J = 8 and J = 6.4 and J = 6.4 Hz,
2H, -CH2-
3.61 ppm; m, 2H, —CH 2 —O—
3.82 ppm; s, 6H, —O—CH 3
3.98 ppm; t, J = 8 Hz, 1H, −CH =
5.53 ppm; s, 2H, phenolic-OH
6.70 ppm; d, J = 2 Hz, 2H, aromatic-H (2-position)
6.76 ppm; dd, J = 8 and J = 2 Hz, 2H, aromatic-H (6-position)
6.84 ppm; d, J = 8 Hz, 2H, aromatic-H (5-position)

13C-NMR (including DEPT measurement) (CDCl3 solvent)
38.759 ppm; -CH2-
46.749 ppm; -CH-
55.917 ppm; -O-CH3
61.234 ppm; —CH 2 —O—
110.443 ppm; aromatic C—H
114.298 ppm; aromatic C—H
120.200 ppm; aromatic C—H
136.817 ppm; aromatic C- (substituted)
144.118 ppm; aromatic C- (substituted)
146.586 ppm; aromatic C- (substituted)

[Example 2. Method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol using hydrochloric acid as an acid catalyst]
To a 50 ml round bottom flask, 10 g of water and 0.43 g of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol were added and dissolved at room temperature. To this round bottom flask, 0.16 g of 10% W / W hydrochloric acid aqueous solution was added and reacted at 65 ° C. for 22.5 hours. After the reaction, it was confirmed that a pale yellow oily substance was released. To this round bottom flask, 0.03 g of potassium carbonate was added to neutralize the hydrochloric acid catalyst.

To the neutralized solution, 3 ml of ethyl acetate was added at room temperature, stirred and the ethyl acetate layer was separated to extract the desired product. This extraction was performed twice. The obtained ethyl acetate layer was dried under reduced pressure to obtain 0.36 g of the target product in a viscous liquid state. The purity of this target product was measured using HPLC in the same manner as in Example 1. As a result, the area percentage without sensitivity correction was 54%.

Example 3. Purification of 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol
The entire amount of the target product containing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol in crude state obtained in Example 2 was subjected to column purification as follows.

As the column, a glass column with a cock (inner diameter) 21 mm × (length) 15 cm packed with Wakogel C-200 was used. To a column packed with toluene at room temperature, 0.36 g of the target product was dissolved and supplied in a mixed solvent consisting of 10 ml of ethyl acetate and 10 ml of toluene. The supply took 15 minutes. Thereafter, the mixture was developed with a mixed solvent of ethyl acetate: toluene = 2: 3 (volume) at a flow rate of 2.5 ml / min to obtain 20 ml fractions. Each fraction was analyzed with a thin layer chromatograph to identify and collect the fraction containing the desired product. The developing solvent was distilled off from the collected fractions under reduced pressure to obtain 0.18 g of the desired purified product of 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol. The properties of the obtained purified product were in a semi-solid state, and the HPLC purity was 93% as an area percentage without sensitivity correction.

[Example 4. Method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol using hydrochloric acid as an acid catalyst (2)]
To a 10 ml capacity test tube, 1 g of dioxane, 1 g of water and 67 mg of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol were added and dissolved at room temperature. When 32.5 mg of 10% W / W hydrochloric acid aqueous solution was added to the test tube and reacted at 75 ° C. for 7 hours and at 85 ° C. for 3 hours, a homogeneous reaction solution colored pale brown was obtained. Analysis by HPLC as in Example 1 confirmed that 24 mg of 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol was contained in this reaction solution. The yield corresponds to 46%.

[Example 5. Method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol using methyl ethyl ketone as a solvent]
To a 10-ml test tube, 5 g of methyl ethyl ketone and 0.30 g of 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol were added and dissolved at room temperature. To this test tube, 78 mg of methanesulfonic acid was added and reacted at room temperature for 23 hours. To this, 0.81 g of a 1N sodium hydroxide aqueous solution was added to neutralize the methanesulfonic acid catalyst. From this, the solvent methyl ethyl ketone was distilled off under reduced pressure, and 6 ml of ethyl acetate was added to the residue, and the resulting solution was washed twice with 5 ml of water. When ethyl acetate was distilled off under reduced pressure, 0.21 g of a light brown viscous liquid was obtained, and the analysis by HPLC had a purity of 64% without sensitivity correction.

[Reference Example 1.3, Method for Producing Cured Resin Using 3-Bis (4-hydroxy-3-methoxyphenyl) -1-propanol]
100 mg of 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol purified product obtained in Example 3, 100 mg of 2,2-bis (4-glycidyloxyphenyl) propane and a curing accelerator When 4 mg of triphenylphosphine was kneaded on a glass plate, a viscous liquid was obtained. When this liquid was applied to an aluminum foil and heated on a hot plate at 110 ° C. for 10 minutes, a yellow-colored high hardness cured resin was obtained.

The present invention is 3,3-bis (4-hydroxy-3-methoxyphenyl), which is an industrially useful bisphenol as a raw material for phenol resin, epoxy resin, epoxy resin curing agent, polycarbonate, polyester, urethane resin and the like. The present invention relates to -1-propanol and a method for producing the same.

Claims (3)

Formula (III) below
(III)
3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol represented by By contacting 1- (4-hydroxy-3-methoxyphenyl) -1,3-propanediol with an acid catalyst, 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol is obtained. A method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol, comprising a step of obtaining. An acid selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, potassium monosulfate, sodium monosulfate, monobasic potassium phosphate, formic acid, acetic acid and oxalic acid The method for producing 3,3-bis (4-hydroxy-3-methoxyphenyl) -1-propanol according to claim 2, which is a catalyst.