GB817000A - Improvements in the production of esters of beta-substituted glycidic acid - Google Patents
Improvements in the production of esters of beta-substituted glycidic acidInfo
- Publication number
- GB817000A GB817000A GB7548/58A GB754858A GB817000A GB 817000 A GB817000 A GB 817000A GB 7548/58 A GB7548/58 A GB 7548/58A GB 754858 A GB754858 A GB 754858A GB 817000 A GB817000 A GB 817000A
- Authority
- GB
- United Kingdom
- Prior art keywords
- beta
- acid
- ester
- alpha
- sodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 11
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 title abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 10
- 239000002253 acid Substances 0.000 abstract 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 7
- 229910052708 sodium Inorganic materials 0.000 abstract 7
- 239000011734 sodium Substances 0.000 abstract 7
- 239000004808 2-ethylhexylester Substances 0.000 abstract 5
- -1 alcohol radical Chemical class 0.000 abstract 5
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 2
- QZBQQHUYQKGPLQ-UHFFFAOYSA-N 2-ethylhexyl 2-chloroacetate Chemical compound CCCCC(CC)COC(=O)CCl QZBQQHUYQKGPLQ-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 abstract 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical class CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 abstract 1
- PYLMCYQHBRSDND-UHFFFAOYSA-N 2-ethyl-2-hexenal Chemical compound CCCC=C(CC)C=O PYLMCYQHBRSDND-UHFFFAOYSA-N 0.000 abstract 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 abstract 1
- CRHQOSXUXQSUQY-UHFFFAOYSA-N 2-ethylhexyl oxirane-2-carboxylate Chemical compound CCCCC(CC)COC(=O)C1CO1 CRHQOSXUXQSUQY-UHFFFAOYSA-N 0.000 abstract 1
- HALONVPKHYIEQU-UHFFFAOYSA-N 3-phenyloxirane-2-carboxylic acid Chemical compound OC(=O)C1OC1C1=CC=CC=C1 HALONVPKHYIEQU-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- IBFHBLOKQVCABG-UHFFFAOYSA-N cyclohexyl 2-chloroacetate Chemical compound ClCC(=O)OC1CCCCC1 IBFHBLOKQVCABG-UHFFFAOYSA-N 0.000 abstract 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- OKWGMWNSHCOYJE-UHFFFAOYSA-N nonyl 2-chloroacetate Chemical compound CCCCCCCCCOC(=O)CCl OKWGMWNSHCOYJE-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 125000000075 primary alcohol group Chemical group 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of beta-substituted glycidic acid are produced by condensing an alpha-halogencarboxylic acid ester with a carbonyl compound in the pressure of a condensing agent comprising a sodium or potassium alcoholate of a primary or secondary alcohol having at least 5 carbon atoms in the molecule and which is difficulty soluble or practically insoluble in water. Suitable alcoholates are those of pentanols, hexanols, cyclohexanols, heptanols, octanols and nonanols, which may be branched with aliphatic or araliphatic side chains and which preferably have the hydroxy group in the alpha or beta position. The said alcoholates are preferably used in 20 to 50 per cent solution in the alcohol corresponding to the alcoholate. Suitable alpha-halogencarboxylic acid esters are the esters of monochloracetic acid, alpha-halogenpropionic acid, alpha-halogen-butyric acids or alpha-halogen-substituted araliphatic carboxylic acids, e.g. alpha-halogenphenylacetic acid. In general the alcohol moiety of the ester corresponds to the alcoholate used, but in the case where esters of other alcohols are used, ester interchange may take place during the process to give the glycidic ester of the alcohol corresponding to the alcoholate. Suitable carbonyl components are acetone, ethyl methyl ketone, cyclohexanone, benzophenone, acetophenone, butyraldehyde, benzaldehyde, furfural, 2-ethylhexanal and 2-ethylhexenal. The reaction may be effected by allowing the alpha-halogen carboxylic acid ester and the carbonyl compound to flow into a solution of the condensing agent at a temperature between - 10 DEG and +20 DEG C., preferably at 0 DEG to 8 DEG C. A diluent such as benzene, toluene, or cyclohexane may be present. In examples: (1) beta, beta-dimethylglycidic acid 2 - ethylhexyl ester is obtained by reacting monochloracetic acid 2-ethylhexyl ester with acetone at 5 DEG C. in a solution of sodium 2-ethylhexylate in 2-ethylhexanol; (2) beta, beta-cyclohexylideneglycidic acid 2-ethylhexyl ester is obtained by reacting monochloracetic acid 2-ethylhexyl ester with cyclohexanone at 5 DEG C. in a solution of sodium 2-ethylhexylate in 2-ethylhexanol; the following esters are prepared in a similar manner using the alcoholate corresponding to the alcohol radical of the ester: alpha-methyl-beta, beta - cyclohexylideneglycidic acid 2 - ethylhexyl ester; beta - phenylglycidic acid 2 - ethylhexyl ester; beta - (n - heptene - D - 3,4-yl-3) glycidic acid 2-ethylhexyl ester; beta-(n-heptyl - 3) - glycidic acid and 2 - ethylhexyl ester, beta, beta - cyclohexylideneglycidic acid n - hexyl ester; beta, beta-cyclohexylidene 2-ethylbutyl ester; beta, beta-cyclohexylidene-3-methylhexyl ester; beta, beta-cyclohexylideneglycidic acid n-octyl ester; (3) beta, betacyclohexylideneglycidic acid cyclohexyl ester is obtained from cyclohexanone and cyclohexyl monochloracetate with sodium cyclohexylate in cyclohexanol; (4) beta, beta-cyclohexylidene glycidic acid 2-ethylhexyl ester is obtained from cyclohexanone and ethyl monochloracetate with sodium 2-ethylhexylate in 2-ethylhexanol with interchange of ester radicals; (5) beta, beta-dimethylglycidic acid 2-ethylhexyl ester is obtained from acetone and ethyl monochloracetate with sodium 2-ethylhexylate in 2-ethylhexanol; (6) beta, beta-cyclohexylideneglycidic acid nonyl ester is obtained from cyclohexanone and nonyl monochloracetate (obtained by esterification of monochloracetic acid with a mixture of isomeric nonanols obtained by the oxoprocess from octenes) with a mixture of the corresponding sodium nonylates in the nonanols.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE817000X | 1957-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB817000A true GB817000A (en) | 1959-07-22 |
Family
ID=6735131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7548/58A Expired GB817000A (en) | 1957-11-07 | 1958-03-10 | Improvements in the production of esters of beta-substituted glycidic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB817000A (en) |
-
1958
- 1958-03-10 GB GB7548/58A patent/GB817000A/en not_active Expired
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