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GB2072174A - Naphtholic compounds - Google Patents

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GB2072174A
GB2072174A GB8108315A GB8108315A GB2072174A GB 2072174 A GB2072174 A GB 2072174A GB 8108315 A GB8108315 A GB 8108315A GB 8108315 A GB8108315 A GB 8108315A GB 2072174 A GB2072174 A GB 2072174A
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compound
naphthol
necessary atoms
compounds
hydrogen
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GB2072174B (en
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3M Co
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Minnesota Mining and Manufacturing Co
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/407—Development processes or agents therefor
    • G03C7/413—Developers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with at least one hydroxy group on a condensed ring system containing two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
    • C07C50/14—Quinones the quinoid structure being part of a condensed ring system containing two rings with unsaturation outside the ring system, e.g. vitamin K1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel compounds suitable for use as dye-forming developing agents in photographic systems which yield coloured dyes upon oxidation, the compounds having the general formula: <IMAGE> in which either R<13> represents hydrogen and R<11> and R<12> independently represent alkyl or aryl or together represent the necessary atoms to form a multiring system, or R<13> represents the necessary atoms to complete a dimer molecule and R<11> and R<12> are as defined above or may additionally represent a hydrogen atom.

Description

SPECIFICATION Novel naphtholic compounds and their preparation This invention relates to novel naphtholic compounds and to their preparation. In particular the invention relates to a group of naphtholic compounds which are suitable for use as dye-forming developing agents in photographic systems.
Ourcopending P.C.T Patent Application No. US 81/00331 which claims priority from British Patent Application No. 8008984 discloses developer solutions, a photographic process and photographic elements in which dye-forming developing agents are present so that during processing of the exposed silver halide they undergo a reaction involving oxidation to produce a dye which amplifies the silver image. Accordingly, it is possible to reduce the silver content of photographic films and obtain the same optical density by utilizing the dye-forming developing agents. By a suitable choice of dyeforming developing agents a wide range of coloured images may be obtained upon processing.
It is an object of the present invention to provide compounds which have utility as dye-forming developing agents.
Therefore according to the present invention there is provided a compound of the general formula:
in which either P13 represents hydrogen and R11 and R12 independently represent alkyl or aryl or together represent the necessary atoms to form a multi-ring system.
or R13 represents the necessary atoms to complete a dimer molecule, and P11 and R12 are as defined above or may additionally represent a hydrogen atom.
The compounds of the invention produce orange-red coloured dyes upon oxidation. The compounds of the invention are suitable for use as dye-forming developing agents in the invention disclosed in the above-mentioned copending Patent Application.
In the general formula (1) when R13 is hydrogen, R11 and R12 may be selected from alkyl, generally having up to 12 carbon atoms and preferably lower alkyl having up to 4 carbon atoms, or aryl, e.g.
phenyl and naphthyl which may be substituted. Alternatively, R11 and R12 together may represent the necessary atoms to form a multi-ring system together with the carbon atom to which they are attached.
Examples of multi-ring systems include fluorenyl, dibenzosuberyl, dibenzotropyl and xanthyl.
R13 may represent the necessary atoms to complete a dimer molecule i.e. R'3 is identical to the nucleus to which it is attached. In such bis-compounds, R11 and R12 are as defined above or may additionally represent a hydrogen atom.
The naphthalene nucleus of the compounds of general formula (1) may optionally possess other substituents, e.g. OH in the 7-position.
The mode of preparation of the compounds of formula (1 ) depends upon the particular substituents.
When R'3 is hydrogen the compounds may be prepared by electrophilic substitution of a-naphthol by stabilized carbonium ions, e.g. from aromatic alcohols:
The his-naphthols may be prepared by reduction of the dinapthoquinone dyes obtained by oxidative coupling of the 2-sub#ituted 1 -naphthol with lead dioxide in acetic acid:
The following Table 1 reports compounds of general formula (1) in accordance with the invention together with their mode of preparation.
TABLE 1
No. Compound Preparation 1 2-(9-fluorenyl)-1-naphthol see Example 1 2 2-diphenylmethyl-1-naphthol see Example 2 3 2-(1-pheny lethy 1)-I -naphthol adding a-pheny lethy la Icohol to a solution of a-naphthol in glacial HOAc containing H2 SO4 4 3,3 ',-di(9-fluoreny l)-4, 4 ',-d ihydroxy- reducing the dye obtained by 1,1 biphenyl adding lead dioxide toa solution of 2-gluorenyl-1- naphthol in HOAc 5 3,3'-di-diphenylmethyl-4,4'- see Example 3 dihydroxy-l , 1 '-biphenyl 6 2-(4-methoxyphenethy 1)-1-naphthol see Example 4 7 2-biphenethyl-1-naphthol see Example 5 8 2-[1-(2-naphthyl)ethyl]-1-naphthol see Example 6 9 2-diphenylmethyl-I ,7 < Iihydroxy see Example 7 naphthalene 10 2-(9dibenzosuberyl)-1-naphthol adding dibenzosuberol to a stirred solution of a-naphthol in glacial HOAc containing H2 804 11 2-(9-d ibenzotropy I)-l-naphthol adding dibenzotropy l-alcohol to a solution of a-naphthol in HOAc containing H2 804 12 1,1 '-dihydroxy-2,2'-dibenzyl- reducing the dye obtained by 4,4'dinaphthyl adding lead dioxide to a solution of 2-benzyl-1 naphthol in HOAc 13 1,1 '-dihydroxy-2,2'-dimethyl- reducing the dye obtained by 4,4'-dinaphthyl oxidation of 2-methyl-1- naphthol by alkaline potassium ferricyanide 14 2-(9-xanthyl)-1-naphthol adding xanthyl alcohol to a solution of a-naphthol in HOAc containing H2 804 The following Table 2 reports the characteristics of certain of the compounds recorded in Table 1 together with the colour of the dyes obtained on oxidation by silver chloride. It will be noted that the compounds of the invention provide orange-red dyes upon oxidation which are suitable for use in amplifying the silver image in photographic elements.
TABLE 2
Data Compound IR v (cm"'1) Colour of dye No, melting point (m.p.) upon oxidation 1 3500, 1575, 1440, 1375, 935 orange-red 2 3510, (OH), 3050, 3020, 1585. 1380 orange-red 3 orange-red 4 orange-red 5 3530 (OH) 1595, 1370 orange-red 6 orange-red 7 orange-red 8 3530, 3504, 3052, 3014, 2970 orange-red 9 3340 (OH), 1600 orange-red 10 3485, 3050, 3010, 2927 orange-red 12 orange-red 13 orange-red The invention will now be illustrated by the following Examples.
EXAMPLE 1 Compound No. 1 - 2-(94luorenyl)-1 -naphthol To a stirred solution of 4 g of a-naphthol (0.028 mole) in 100 ml glacial acetic acid was added 5 ml concentrated sulphuric acid.3.64 g (0.02 mole) of 9-fíuorenol was then added portionwise over 30 minutes. The mixture was stirred at room temperature for 3 hours, poured over water and extracted with ether. The ethereal extract was washed repeatedly with diluted NaOH solution to remove unreacted a-naphthol, dried over CaCI2 and evaporated. Residue was taken up in chloroform, chilled in ice and filtered. The filtrate was evaporated, leaving an oil.
Yield 5.6 g (84%) based on 9-fluorenol.
lRcm#1:3500, 1575,1440,1375,935.
EXAMPLE 2 Compound No. 2 - 2-diphenylmethyl-1 -naphthol 9.2 g benzhydrol (0.05 mole) was added portionwise over 30 mins to a stirred solution of 10 g (0.07 mole) -naphthol in 150 ml glacial acetic acid containing 5 ml concentrated sulphuric acid. The mixture was stirred at room temperature for 4 hours, poured over water, extracted with ether. The ethereal extract was washed repeatedly with dilute NaOH solutions, dried over CaC12 and evaporated.
Residue was taken up in chloroform, chilled in ice and the crystalline precipitate filtered. The filtrate was evaporated, leaving an oil.
Yield 11 g (71 %) IR (cm~'): 3510,3050,3020, 1585.
EXAMPLE 3 Compound No. 5 - 3,3'-bisdiphenylmethyl-4,4'-dihydroxy-1 ,1 '-dinaphthyl A. 3,3'-bisdiphenylmethyl-p-dinaphthoquinone.
To a stirred solution of 6.2 g (0.02 mole) 2-diphenylmethyl-1 -naphthol in 100 ml glacial acetic acid at room temperature was added portionwise over 10 mins. 4.8 g lead dioxide. The solution was chilled in ice at the onset of the exothermic reaction and continued to be stirred in ice water for 1 hour.
Water was added and the red brown precipitate was filtered, washed repeatedly with distilled water, twice with cold methanol and dried.
Yield 5.8 g (93.5%) IR (cm~'): 1620, 1 586, 1276.
B. 3,3'-bisdiphenylenethyl-4,4'-dihydroxy-1 1 '-dinaphthyl.
Zinc dust was added portionwise to a stirred suspension of 4 g 3,3'-bisphenylmethyl-pdinaphthoquinone at 400C until the colour discharged. The colourless solution was filtered. The precipitate was washed repeatedly with distilled water and dried.
Yield 3.7 g yellow powder (92.5%) IR (cm~'): 3530 (OH), 1595, 1370 EXAMPLE 4 Compound No. 6 - 2- [ 1 -(4-methoxyphenyl)ethylj-1 -naphthol To a stirred solution of 10 g of a-naphthol (0.07 mole) in 150 ml glacial acetic acid at room temperature was added 5 ml concentrated sulphuric acid. 7.6 g of p-methoxyphenethylalcohol (0.05 mole) was added dropwise over 30 minutes. The mixture was stirred at room temperature for 4 hours, poured over water and extracted with ether.
The ethereal extract was washed repeatedly with diluted NaOH solutions, dried over CaCI2 and evaporated. Residue chromatographed over alumina. Elution with petroleum ether-ether 2:1 gave an oil Yield 12.5 g (90%)
Cl9HlsO2 C % | H % | O % Calculated 82.0 6.4 11.5 Found 82.4 5.8 EXAMPLE 5 Compound No. 7 - 2-( 1 -biphenylethyl)- 1 -naphthol To a stirred solution of 10 g a-naphthol (0.07 mole) in 1 50 ml glacial acetic acid containing 5 ml concentrated sulphuric acid was added portionwise 9.9 g of biphenylethyl alcohol (0.05 mole) over 30 minutes. The mixture was stirred at room temperature for 4 hours, poured over water and extracted with ether.The ethereal extract was washed repeatedly with diluted NaOH solution, dried over CaCI2 and evaporated. The residue was chromatographed over alumina, elution with hexane-ether 2:1 gave a yellowish oil.
Yield 15g(91%).
s C24H20O C% H% 0% Calculated 88.9 6.2 4.9 Found 89.1 6.33 EXAMPLE 6 Compound No. 8 - 2- [ 1 -(2-naphthyl)-ethyl]-1 -naphthol 8.6 g of 1 -(2-naphthyl)-ethanol (0.05 mole) was added portionwise over 30 minutes to a stirred solution of 10 g of a-naphthol in 1 50 ml of glacial acetic acid containing 5 ml of concentrated sulphuric acid. The mixture was stirred at room temperature for 4 hours, poured over water and extracted with ether. The ethereal extract was washed repeatedly with diluted NaOH solution, dried and evaporated.
The residue was taken up in chloroform chilled in ice, filtered, evaporated and chromatographed over alumina. Elution with hexane-ether 2:1 gave an oil.
Yield 6.5 g.
IR cm~': 3530,3504,3052,3014, 2970.
NMR (a): 1.67 (CH3, doublet, 3H), 4.47 (CH, quartet, 1 H). 5.22 (OH, singlet, 1 H), 6.9-8.2 (ArH, multiplet, 13H).
C22HlsO C% HO/o 0% Calculated 88 6 6.04 5437 Found 89.3 5.7 EXAMPLE 7 Compound No. 9 -- 2-diphenylmethyl-l ,7-dihydroxynaphthalene 3.7 g benzhydrol (0.02 mole) was added portionwise over 20 mins to a stirred solution of 4 g 1,7dihydroxynaphthalene in 50 ml HOAc at room temperature. Mixture was stirred for 3 hours, poured over water, extracted with ether. The ethereal extract was washed repeatedly with dilute NaOH solution, water, dried over CaCI2, evaporated leaving an oil which is then taken up in CHCI, and left in fridge. The CHCI, solution was filtered evaporated, leaving an oil.
Yield 5.3 g (81%).

Claims (11)

1. A compound of the general formula:
in which either R13 represents hydrogen and R11 and R12 independently represent alkyl or aryl or together represent the necessary atoms to form a multi-ring system, or R13 represents the necessary atoms to complete a dimer molecule and R11 and R12 are as defined above or may additionally represent a hydrogen atom.
2. A compound as claimed in Claim 1 in which R1' is lower alkyl and R12 is aryl.
3. A compound as claimed in Claim 2 in which R12 is phenyl or naphthyl each of which may be substituted.
4. A compound as claimed in Claim 1 in which R11 and R12 represents the necessary atoms to complete a fluorenyl, dibenzosuberyl, dibenzotropyl or xanthyl ring system.
5. A compound as claimed in any preceding claim in which R13 is hydrogen.
6. A compound as claimed in any one of Claims 1 to 4, in which R'3 represents the necessary atoms to complete a bis compound.
7. A compound as claimed in Claim 1 having the structure of any one of Compound Nos. 1 to 14 reported in Table 1 herein.
8. A compound as claimed in Claim 1 substantially as herein described with reference to any one of the Examples.
9. A method of preparing a compound as claimed in Claim 1 in which R3 is hydrogen, comprising the following reaction:
10. A method of preparing a bis-naphthol as claimed in Claim 1 which comprises the following reaction:
11. A method of preparing a compound as claimed in Claim 1 substantially as herein described with reference to any one of the Examples.
GB8108315A 1980-03-17 1981-03-17 Naphtholic compounds Expired GB2072174B (en)

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GB8108315A GB2072174B (en) 1980-03-17 1981-03-17 Naphtholic compounds

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4699868A (en) * 1984-03-02 1987-10-13 Minnesota Mining And Manufacturing Company Photographic tanning developer formulation
EP0201071A3 (en) * 1985-05-08 1988-08-10 E.I. Du Pont De Nemours And Company 2-substituted-1-naphthols as 5-lipoxygenase inhibitors
US4879421A (en) * 1988-08-15 1989-11-07 General Electric Company Method for preparing optically active binaphthol and spiroibiindanol
US4985435A (en) * 1985-05-08 1991-01-15 E. I. Du Pont De Nemours And Company 2-substituted-1-naphthols as 5-lipoxygenase inhibitors
AU606034B2 (en) * 1985-05-08 1991-01-31 Du Pont Pharmaceuticals Company 2-substituted -1- naphthols as 5-lipogenase inhibitors
US5026759A (en) * 1985-05-08 1991-06-25 Du Pont Merck Pharmaceutical 2-substituted-1-naphthols as 5-lipoxygenase inhibitors
US5364733A (en) * 1992-07-16 1994-11-15 Minnesota Mining And Manufacturing Company Photothermographic elements with novel layer structures, each of which contains a thermally-diffusible oxidizable leuco dye and process for producing a color image from leuco dye

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4699868A (en) * 1984-03-02 1987-10-13 Minnesota Mining And Manufacturing Company Photographic tanning developer formulation
EP0201071A3 (en) * 1985-05-08 1988-08-10 E.I. Du Pont De Nemours And Company 2-substituted-1-naphthols as 5-lipoxygenase inhibitors
US4833164A (en) * 1985-05-08 1989-05-23 E. I. Du Pont De Nemours And Company 2-substituted-1-naphthols, pharmaceutical compositions of, and their use as 5-lipoxygenase inhibitors
US4985435A (en) * 1985-05-08 1991-01-15 E. I. Du Pont De Nemours And Company 2-substituted-1-naphthols as 5-lipoxygenase inhibitors
US4985442A (en) * 1985-05-08 1991-01-15 E. I. Du Pont De Nemours And Company 2-substituted-1-naphthols as 5-lipoxygenase inhibitors
AU606034B2 (en) * 1985-05-08 1991-01-31 Du Pont Pharmaceuticals Company 2-substituted -1- naphthols as 5-lipogenase inhibitors
US5026759A (en) * 1985-05-08 1991-06-25 Du Pont Merck Pharmaceutical 2-substituted-1-naphthols as 5-lipoxygenase inhibitors
US4879421A (en) * 1988-08-15 1989-11-07 General Electric Company Method for preparing optically active binaphthol and spiroibiindanol
US5364733A (en) * 1992-07-16 1994-11-15 Minnesota Mining And Manufacturing Company Photothermographic elements with novel layer structures, each of which contains a thermally-diffusible oxidizable leuco dye and process for producing a color image from leuco dye

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Effective date: 19940317