JPS5935371B2 - 芳香族酢酸を製造する方法 - Google Patents

芳香族酢酸を製造する方法

Info

Publication number: JPS5935371B2
Authority: JP; Japan
Prior art keywords: acetic acid; aromatic; trichloroethanol; reaction; base
Prior art date: 1978-11-14
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

Application number

JP13936578A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5566524A (en

Inventor

聖近藤

保藤本

稔須田

大英常本

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sagami Chemical Research Institute

Original Assignee

Sagami Chemical Research Institute

Priority date (The priority date 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 date listed.)

1978-11-14

Filing date

1978-11-14

Publication date

1984-08-28

1978-11-14 Application filed by Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute

1978-11-14 Priority to JP13936578A priority Critical patent/JPS5935371B2/ja

1979-11-13 Priority to CA339,767A priority patent/CA1133915A/en

1979-11-13 Priority to EP79104475A priority patent/EP0011279B1/de

1979-11-13 Priority to US06/093,818 priority patent/US4268442A/en

1979-11-13 Priority to AT724779A priority patent/AT370076B/de

1979-11-13 Priority to DE7979104475T priority patent/DE2962737D1/de

1980-05-20 Publication of JPS5566524A publication Critical patent/JPS5566524A/ja

1984-08-28 Publication of JPS5935371B2 publication Critical patent/JPS5935371B2/ja

Status Expired legal-status Critical Current

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 66
125000003118 aryl group Chemical group 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title claims description 4
238000000034 method Methods 0.000 claims description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
239000002585 base Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
239000002798 polar solvent Substances 0.000 claims description 8
150000001298 alcohols Chemical class 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 2
-1 aromatic acetic acids Chemical class 0.000 description 27
235000011054 acetic acid Nutrition 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 17
239000002994 raw material Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 7
229960001760 dimethyl sulfoxide Drugs 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
150000003934 aromatic aldehydes Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
NIBKDWIGIKUFKL-UHFFFAOYSA-N 1,2,2-trichloroethanol Chemical compound OC(Cl)C(Cl)Cl NIBKDWIGIKUFKL-UHFFFAOYSA-N 0.000 description 2
SDKGVVKRGMXYEN-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-methoxycyclohexa-2,4-dien-1-yl)ethanol Chemical compound ClC(Cl)(Cl)C(O)C1(OC)CC=CC=C1 SDKGVVKRGMXYEN-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000007259 addition reaction Methods 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
238000007142 ring opening reaction Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000002195 soluble material Substances 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
MDKKIWAFYRCBAF-UHFFFAOYSA-N (1,1,1-trichloro-2-phenylpropan-2-yl) hypochlorite Chemical compound ClOC(C)(C(Cl)(Cl)Cl)C1=CC=CC=C1 MDKKIWAFYRCBAF-UHFFFAOYSA-N 0.000 description 1
QYYGVYVEFZIQMT-UHFFFAOYSA-N 1-(7ah-1,3-benzodioxol-3a-yl)-2,2,2-trichloroethanol Chemical compound C1=CC=CC2(C(C(Cl)(Cl)Cl)O)C1OCO2 QYYGVYVEFZIQMT-UHFFFAOYSA-N 0.000 description 1
GHKMHTPUCGIFFD-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-chlorocyclohexa-2,4-dien-1-yl)ethanol Chemical compound ClC(Cl)(Cl)C(O)C1(Cl)CC=CC=C1 GHKMHTPUCGIFFD-UHFFFAOYSA-N 0.000 description 1
UOOFMLWWQLOBPZ-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-ethoxycyclohexa-2,4-dien-1-yl)ethanol Chemical compound CCOC1(C(O)C(Cl)(Cl)Cl)CC=CC=C1 UOOFMLWWQLOBPZ-UHFFFAOYSA-N 0.000 description 1
CCTXCHOODFXFBH-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-ethylcyclohexa-2,4-dien-1-yl)ethanol Chemical compound ClC(Cl)(Cl)C(O)C1(CC)CC=CC=C1 CCTXCHOODFXFBH-UHFFFAOYSA-N 0.000 description 1
SBYOXRZVFTXIDQ-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-methylcyclohexa-2,4-dien-1-yl)ethanol Chemical compound ClC(Cl)(Cl)C(O)C1(C)CC=CC=C1 SBYOXRZVFTXIDQ-UHFFFAOYSA-N 0.000 description 1
YCLOGOWNWZFPBP-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-phenoxycyclohexa-2,4-dien-1-yl)ethanol Chemical compound C=1C=CC=CC=1OC1(C(C(Cl)(Cl)Cl)O)CC=CC=C1 YCLOGOWNWZFPBP-UHFFFAOYSA-N 0.000 description 1
DOVJIHWJPNZDAB-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-phenylcyclohexa-2,4-dien-1-yl)ethanol Chemical compound C=1C=CC=CC=1C1(C(C(Cl)(Cl)Cl)O)CC=CC=C1 DOVJIHWJPNZDAB-UHFFFAOYSA-N 0.000 description 1
JMHSLIYTHASXFX-UHFFFAOYSA-N 2,2,2-trichloro-1-(1-phenylmethoxycyclohexa-2,4-dien-1-yl)ethanol Chemical compound C=1C=CC=CC=1COC1(C(C(Cl)(Cl)Cl)O)CC=CC=C1 JMHSLIYTHASXFX-UHFFFAOYSA-N 0.000 description 1
ABFRBTDJEKZSRM-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanol Chemical compound ClC(Cl)(Cl)C(O)C1=CC=CC=C1 ABFRBTDJEKZSRM-UHFFFAOYSA-N 0.000 description 1
QBMTZEDLUUIISP-UHFFFAOYSA-N 2,2,2-trichloro-1-thiophen-2-ylethanol Chemical compound ClC(Cl)(Cl)C(O)C1=CC=CS1 QBMTZEDLUUIISP-UHFFFAOYSA-N 0.000 description 1
KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
GFXQHKOMQWWCLI-UHFFFAOYSA-N 2-(4-methylphenyl)-2-methylsulfanylacetic acid Chemical compound CSC(C(O)=O)C1=CC=C(C)C=C1 GFXQHKOMQWWCLI-UHFFFAOYSA-N 0.000 description 1
GXXXUZIRGXYDFP-UHFFFAOYSA-N 2-(4-methylphenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-N 0.000 description 1
ZSTBZBURMWJKSQ-UHFFFAOYSA-N 2-diazonio-1-phenylethenolate Chemical compound N#[N+]C=C([O-])C1=CC=CC=C1 ZSTBZBURMWJKSQ-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
150000007960 acetonitrile Chemical class 0.000 description 1
230000000397 acetylating effect Effects 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000005171 halobenzenes Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000003607 modifier Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000004904 shortening Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229940029273 trichloroacetaldehyde Drugs 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

JP13936578A 1978-11-14 1978-11-14 芳香族酢酸を製造する方法 Expired JPS5935371B2 (ja)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
JP13936578A JPS5935371B2 (ja)	1978-11-14	1978-11-14	芳香族酢酸を製造する方法
CA339,767A CA1133915A (en)	1978-11-14	1979-11-13	Process for preparing aromatic acetic acids
EP79104475A EP0011279B1 (de)	1978-11-14	1979-11-13	Verfahren zur Herstellung aromatisch substituierter Essigsäuren
US06/093,818 US4268442A (en)	1978-11-14	1979-11-13	Process for preparing aromatic acetic acid
AT724779A AT370076B (de)	1978-11-14	1979-11-13	Verfahren zur herstellung von arylessigsaeuren
DE7979104475T DE2962737D1 (en)	1978-11-14	1979-11-13	Process for the preparation of aromatically substituted acetic acids

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP13936578A JPS5935371B2 (ja)	1978-11-14	1978-11-14	芳香族酢酸を製造する方法

Publications (2)

Publication Number	Publication Date
JPS5566524A JPS5566524A (en)	1980-05-20
JPS5935371B2 true JPS5935371B2 (ja)	1984-08-28

Family

ID=15243623

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP13936578A Expired JPS5935371B2 (ja)	1978-11-14	1978-11-14	芳香族酢酸を製造する方法

Country Status (3)

Country	Link
JP (1)	JPS5935371B2 (de)
AT (1)	AT370076B (de)
CA (1)	CA1133915A (de)

1978
- 1978-11-14 JP JP13936578A patent/JPS5935371B2/ja not_active Expired
1979
- 1979-11-13 AT AT724779A patent/AT370076B/de active
- 1979-11-13 CA CA339,767A patent/CA1133915A/en not_active Expired

Also Published As

Publication number	Publication date
AT370076B (de)	1983-02-25
CA1133915A (en)	1982-10-19
ATA724779A (de)	1982-07-15
JPS5566524A (en)	1980-05-20

Publication	Publication Date	Title
US3991106A (en)	1976-11-09	16-Ethers of 8-aza-9-dioxothia-11,12-seco-prostaglandins
EP0011279B1 (de)	1982-05-05	Verfahren zur Herstellung aromatisch substituierter Essigsäuren
US4126629A (en)	1978-11-21	Substituted phenoxy-tridecenoic acids/esters
PL133927B1 (en)	1985-07-31	Process for preparing alkanocarboxylic acids substituted in position alpha with aromatic group or their esters
JPS5935371B2 (ja)	1984-08-28	芳香族酢酸を製造する方法
US4237298A (en)	1980-12-02	Aromatic acetic acid derivatives having sulfur atom at alpha-position and process for their preparation
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JPS5935370B2 (ja)	1984-08-28	芳香族酢酸の製造方法
FR2497200A1 (fr)	1982-07-02	Composes d'acide fluoromethylthioacetique
EP0037327A1 (de)	1981-10-07	Substituierte Derivate der 3-Formyl-4-methylpentansäure, ihre Herstellung und ihre Anwendung bei der Herstellung substituierter 3-Formyl-but-3-ene-1-säure
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CA1160245A (en)	1984-01-10	Antihypertensive polyhalohydroxyisopropyl phenylalkanoic and phenylalkenoic acids, amides and esters and intermediates thereto
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JPH0341456B2 (de)	1991-06-24
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