SU1075971A3 - Способ получени 5-(2,4-дифторфенил)-салициловой кислоты - Google Patents
Способ получени 5-(2,4-дифторфенил)-салициловой кислоты Download PDFInfo
- Publication number
- SU1075971A3 SU1075971A3 SU802999196A SU2999196A SU1075971A3 SU 1075971 A3 SU1075971 A3 SU 1075971A3 SU 802999196 A SU802999196 A SU 802999196A SU 2999196 A SU2999196 A SU 2999196A SU 1075971 A3 SU1075971 A3 SU 1075971A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- palladium
- palladium catalyst
- acid
- molar weight
- anions
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 19
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 7
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 6
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 claims description 6
- 229960001047 methyl salicylate Drugs 0.000 claims description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- -1 ace tat anions Chemical class 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- 230000001172 regenerating effect Effects 0.000 claims description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 abstract 1
- 230000008929 regeneration Effects 0.000 abstract 1
- 238000011069 regeneration method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000021523 carboxylation Effects 0.000 description 3
- 238000006473 carboxylation reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- SJMMFGNAJFFWNL-UHFFFAOYSA-N (2,4-difluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C=C1F SJMMFGNAJFFWNL-UHFFFAOYSA-N 0.000 description 1
- UVNBLIFEQQFJMM-UHFFFAOYSA-N 2,4-difluorobenzenediazonium Chemical compound FC1=CC=C([N+]#N)C(F)=C1 UVNBLIFEQQFJMM-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- 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 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- HSNVNALJRSJDHT-UHFFFAOYSA-N P(=O)(=O)[Mo] Chemical compound P(=O)(=O)[Mo] HSNVNALJRSJDHT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- BEWZPBWLGIPWFP-UHFFFAOYSA-N [V].P(=O)(=O)[Mo] Chemical compound [V].P(=O)(=O)[Mo] BEWZPBWLGIPWFP-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HENZRBYHAMWFGX-UHFFFAOYSA-N carbonic acid;ethanamine Chemical compound CC[NH3+].OC([O-])=O HENZRBYHAMWFGX-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- QMPIMDAYFIIMIH-UHFFFAOYSA-N methyl 5-(2,4-difluorophenyl)-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC(C=2C(=CC(F)=CC=2)F)=C1 QMPIMDAYFIIMIH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/090,792 US4237315A (en) | 1979-11-02 | 1979-11-02 | Preparation of 5(halophenyl)salicylic acid compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1075971A3 true SU1075971A3 (ru) | 1984-02-23 |
Family
ID=22224332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802999196A SU1075971A3 (ru) | 1979-11-02 | 1980-10-31 | Способ получени 5-(2,4-дифторфенил)-салициловой кислоты |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4237315A (OSRAM) |
| EP (1) | EP0028407B1 (OSRAM) |
| JP (1) | JPS5935909B2 (OSRAM) |
| AR (1) | AR229020A1 (OSRAM) |
| AT (1) | ATE4587T1 (OSRAM) |
| AU (1) | AU530586B2 (OSRAM) |
| CA (1) | CA1149410A (OSRAM) |
| CS (1) | CS221934B2 (OSRAM) |
| DD (1) | DD153681A5 (OSRAM) |
| DE (1) | DE3064774D1 (OSRAM) |
| DK (1) | DK156564C (OSRAM) |
| ES (1) | ES496444A0 (OSRAM) |
| FI (1) | FI68610C (OSRAM) |
| GR (1) | GR70785B (OSRAM) |
| HU (1) | HU182226B (OSRAM) |
| IE (1) | IE50334B1 (OSRAM) |
| NO (1) | NO152555C (OSRAM) |
| NZ (1) | NZ195304A (OSRAM) |
| PL (1) | PL126701B1 (OSRAM) |
| PT (1) | PT71978B (OSRAM) |
| SU (1) | SU1075971A3 (OSRAM) |
| YU (1) | YU41949B (OSRAM) |
| ZA (1) | ZA806723B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4355174A (en) * | 1979-11-02 | 1982-10-19 | Merck & Co., Inc. | Preparation of 5(halophenyl)salicylic acid compounds |
| IT1190926B (it) * | 1982-07-22 | 1988-02-24 | Zambon Spa | Procedimento per preparare l'acido 2',4'-difluoro-4-idrossi-(1,1'-difenil)-3-carbossilico |
| IT1250736B (it) * | 1991-08-01 | 1995-04-21 | Zambon Spa | Processo per la preparazione dell'acido 5-(2',4'-difluorofenil) salicilico in forma ii pura |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL30496A0 (en) * | 1967-08-14 | 1968-10-24 | Merck & Co Inc | Process for the preparation of phenyl salicylic acid compounds and intermediates used therein |
| IL30498A0 (en) * | 1967-08-14 | 1968-10-24 | Merck & Co Inc | Process for the preparation of phenyl salicylic acid compounds and intermediates used therein |
| US3632831A (en) * | 1969-01-03 | 1972-01-04 | Du Pont | Synthesis of dialkyl 4 4'-biphenyldicarboxylates |
-
1979
- 1979-11-02 US US06/090,792 patent/US4237315A/en not_active Expired - Lifetime
-
1980
- 1980-10-20 FI FI803293A patent/FI68610C/fi not_active IP Right Cessation
- 1980-10-20 NZ NZ195304A patent/NZ195304A/xx unknown
- 1980-10-21 AU AU63550/80A patent/AU530586B2/en not_active Ceased
- 1980-10-21 CS CS807122A patent/CS221934B2/cs unknown
- 1980-10-22 YU YU2701/80A patent/YU41949B/xx unknown
- 1980-10-27 DD DD80224759A patent/DD153681A5/de not_active IP Right Cessation
- 1980-10-27 PT PT71978A patent/PT71978B/pt not_active IP Right Cessation
- 1980-10-28 CA CA000363415A patent/CA1149410A/en not_active Expired
- 1980-10-30 GR GR63251A patent/GR70785B/el unknown
- 1980-10-30 PL PL1980227576A patent/PL126701B1/pl unknown
- 1980-10-30 HU HU802621A patent/HU182226B/hu unknown
- 1980-10-31 AR AR283086A patent/AR229020A1/es active
- 1980-10-31 JP JP55152379A patent/JPS5935909B2/ja not_active Expired
- 1980-10-31 EP EP80106705A patent/EP0028407B1/en not_active Expired
- 1980-10-31 NO NO803255A patent/NO152555C/no unknown
- 1980-10-31 DE DE8080106705T patent/DE3064774D1/de not_active Expired
- 1980-10-31 SU SU802999196A patent/SU1075971A3/ru active
- 1980-10-31 ZA ZA00806723A patent/ZA806723B/xx unknown
- 1980-10-31 ES ES496444A patent/ES496444A0/es active Granted
- 1980-10-31 DK DK462180A patent/DK156564C/da not_active IP Right Cessation
- 1980-10-31 AT AT80106705T patent/ATE4587T1/de active
- 1980-10-31 IE IE2261/80A patent/IE50334B1/en not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| 1. Руденко А.И. и др. Исследование по разработке катализаторов окислительного сочетани ароматических соединений. - Кинетика и катализ, т. 18, 4, 1977, с. 915-920. 2.Halden R. Van. Verberg G. The oxidative conpling of aromatic compounds with palladium Salts. . trav. Chim., 84, 1965, 1263-1273. 3.Патент FR № 2288729, кл. С 07 С 65/14, 1976. * |
Also Published As
| Publication number | Publication date |
|---|---|
| AR229020A1 (es) | 1983-05-31 |
| JPS5935909B2 (ja) | 1984-08-31 |
| FI68610C (fi) | 1985-10-10 |
| PT71978A (en) | 1980-11-01 |
| PL227576A1 (OSRAM) | 1981-06-19 |
| NO152555C (no) | 1985-10-16 |
| DE3064774D1 (en) | 1983-10-13 |
| EP0028407A1 (en) | 1981-05-13 |
| ES8107147A1 (es) | 1981-10-01 |
| PT71978B (en) | 1982-03-31 |
| CS221934B2 (en) | 1983-04-29 |
| US4237315A (en) | 1980-12-02 |
| YU270180A (en) | 1983-01-21 |
| PL126701B1 (en) | 1983-08-31 |
| DK462180A (da) | 1981-05-03 |
| DK156564B (da) | 1989-09-11 |
| ATE4587T1 (de) | 1983-09-15 |
| GR70785B (OSRAM) | 1983-03-23 |
| NO152555B (no) | 1985-07-08 |
| AU530586B2 (en) | 1983-07-21 |
| YU41949B (en) | 1988-02-29 |
| FI803293L (fi) | 1981-05-03 |
| DK156564C (da) | 1990-02-12 |
| AU6355080A (en) | 1981-08-20 |
| FI68610B (fi) | 1985-06-28 |
| NZ195304A (en) | 1982-12-07 |
| NO803255L (no) | 1981-05-04 |
| IE50334B1 (en) | 1986-04-02 |
| ZA806723B (en) | 1982-06-30 |
| CA1149410A (en) | 1983-07-05 |
| ES496444A0 (es) | 1981-10-01 |
| IE802261L (en) | 1981-05-02 |
| EP0028407B1 (en) | 1983-09-07 |
| HU182226B (en) | 1983-12-28 |
| DD153681A5 (de) | 1982-01-27 |
| JPS5690037A (en) | 1981-07-21 |
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