GB1160725A - Improvements in the Preparation of Phenylalkanoic Acids - Google Patents

Improvements in the Preparation of Phenylalkanoic Acids

Info

Publication number
GB1160725A
GB1160725A GB52979/66A GB5297966A GB1160725A GB 1160725 A GB1160725 A GB 1160725A GB 52979/66 A GB52979/66 A GB 52979/66A GB 5297966 A GB5297966 A GB 5297966A GB 1160725 A GB1160725 A GB 1160725A
Authority
GB
United Kingdom
Prior art keywords
give
formula
halo
salt
compound
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
Application number
GB52979/66A
Inventor
Raymond Arthur Dytham
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.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure Drug Co Ltd
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.)
Filing date
Publication date
Application filed by Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB52979/66A priority Critical patent/GB1160725A/en
Priority to FI673116A priority patent/FI49414C/en
Priority to NO170658A priority patent/NO131169C/no
Priority to ES347566A priority patent/ES347566A1/en
Priority to AT1065267A priority patent/AT281002B/en
Priority to SE16188/67A priority patent/SE349795B/xx
Priority to CH1655967A priority patent/CH483386A/en
Priority to NL6715993A priority patent/NL6715993A/xx
Priority to FR129491A priority patent/FR1545270A/en
Publication of GB1160725A publication Critical patent/GB1160725A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C07C47/23—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • 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)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lift Valve (AREA)

Abstract

1,160,725. Process for phenylalkanoic acids. BOOTS PURE DRUG CO. Ltd. 20 Nov., 1967 [25 Nov., 1966], No. 52979/66. Heading C2C. A process for the preparation of compounds I in which R is p-R 1 -phenyl (R 1 is C 2-6 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, C 3-4 alkoxy, C 1-5 alkylthio, C 3-4 alkenyloxy, C 3-5 alkenylthio, C 3-7 cycloalkoxy, C 2-7 cycloalkylthio, phenoxy or phenylthio) or the group wherein R 2 and R 3 are similar or different and represent, H, halo, alkyl, CF 3 , alkoxy or alkylthio comprises (1) reacting a compound II -RCOCH 3 with a compound of formula halo-CH 2 COOR 4 wherein R 4 is an esterifying group and halo is Cl or Br to give a compound of Formula III (2) hydrolysing the glycidic acid ester to give a salt of Formula V wherein M is a single equivalent of a salt-forming metal; (3) decarboxylating the salt V to give an aldehyde IV of formula R-CH(CH 3 )CHO and (4) oxidizing the aldehyde IV to give acid I. Compounds V are claimed per se. The aldehydes IV are characterized by means of their 2,4-dinitrophenylhydrazine derivatives.
GB52979/66A 1966-11-25 1966-11-25 Improvements in the Preparation of Phenylalkanoic Acids Expired GB1160725A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB52979/66A GB1160725A (en) 1966-11-25 1966-11-25 Improvements in the Preparation of Phenylalkanoic Acids
FI673116A FI49414C (en) 1966-11-25 1967-11-20 Process for the preparation of new, anti-inflammatory salts of substituted 3-phenyl-2,3-epoxybutyric acids.
NO170658A NO131169C (en) 1966-11-25 1967-11-22
ES347566A ES347566A1 (en) 1966-11-25 1967-11-24 Improvements in the Preparation of Phenylalkanoic Acids
AT1065267A AT281002B (en) 1966-11-25 1967-11-24 Process for the production of α- (substituted-phenyl) -propionic acids
SE16188/67A SE349795B (en) 1966-11-25 1967-11-24
CH1655967A CH483386A (en) 1966-11-25 1967-11-24 Process for the preparation of a- (substituted phenyl) propionic acids
NL6715993A NL6715993A (en) 1966-11-25 1967-11-24
FR129491A FR1545270A (en) 1966-11-25 1967-11-24 Process for the preparation of phenylalkanoic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB52979/66A GB1160725A (en) 1966-11-25 1966-11-25 Improvements in the Preparation of Phenylalkanoic Acids

Publications (1)

Publication Number Publication Date
GB1160725A true GB1160725A (en) 1969-08-06

Family

ID=10466133

Family Applications (1)

Application Number Title Priority Date Filing Date
GB52979/66A Expired GB1160725A (en) 1966-11-25 1966-11-25 Improvements in the Preparation of Phenylalkanoic Acids

Country Status (8)

Country Link
AT (1) AT281002B (en)
CH (1) CH483386A (en)
ES (1) ES347566A1 (en)
FI (1) FI49414C (en)
GB (1) GB1160725A (en)
NL (1) NL6715993A (en)
NO (1) NO131169C (en)
SE (1) SE349795B (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2404160A1 (en) * 1973-01-29 1974-08-01 Nisshin Flour Milling Co PROCESS FOR THE PREPARATION OF 2- (4-ALKYLPHENYL) -PROPRIONIC ACID
DE2404159A1 (en) * 1973-01-29 1974-08-29 Nisshin Flour Milling Co PROCESS FOR THE PRODUCTION OF 2-PHENYLPROPIONIC ACID DERIVATIVES
JPS4995936A (en) * 1973-01-29 1974-09-11
JPS50131940A (en) * 1974-04-09 1975-10-18
US3925458A (en) * 1973-01-29 1975-12-09 Nisshin Flour Milling Co Process for preparing 2-(4-alkylphenyl)-propion-aldehyde and propionic acid
DE2533397A1 (en) * 1974-07-29 1976-02-12 Nisshin Flour Milling Co PROCESS FOR THE PREPARATION OF 2-ARYLPROPIONIC ACIDS
JPS5318535A (en) * 1976-08-04 1978-02-20 Ota Pharma Production of 22*4** isobutylphenyl* propionic acid
JPS5318534A (en) * 1976-08-04 1978-02-20 Ota Pharma Production of 22*4** isobutylphenyl* propionic acid
EP0226566A1 (en) * 1985-11-25 1987-06-24 Monsanto Company Oxidation of 2-arylpropanals
EP0545891A2 (en) * 1986-04-07 1993-06-09 Sumitomo Chemical Company, Limited Aldehyde compounds and derivatives thereof useful as intermediates in the preparation of insectical ether compounds
US5260477A (en) * 1988-12-21 1993-11-09 Nippon Petrochemicals Co., Ltd. Method for preparing alpha-(4-isobutylphenyl)propionic acid or its precursor
US5273895A (en) * 1992-10-26 1993-12-28 Sepracor, Inc. Enantioselective production of chiral carboxylic acids
WO1999008989A1 (en) * 1997-08-20 1999-02-25 First Chemical Corporation Processes for preparing hydrocinnamic acid
US6096920A (en) * 1997-01-08 2000-08-01 Albemarle Corporation Preparation of carboxylic compounds and their derivatives

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5335067B2 (en) * 1973-01-29 1978-09-25
DE2404159A1 (en) * 1973-01-29 1974-08-29 Nisshin Flour Milling Co PROCESS FOR THE PRODUCTION OF 2-PHENYLPROPIONIC ACID DERIVATIVES
JPS4995936A (en) * 1973-01-29 1974-09-11
US3925458A (en) * 1973-01-29 1975-12-09 Nisshin Flour Milling Co Process for preparing 2-(4-alkylphenyl)-propion-aldehyde and propionic acid
DE2404160A1 (en) * 1973-01-29 1974-08-01 Nisshin Flour Milling Co PROCESS FOR THE PREPARATION OF 2- (4-ALKYLPHENYL) -PROPRIONIC ACID
US3965161A (en) * 1973-01-29 1976-06-22 Nisshin Flour Milling Co., Ltd. Process of producing a 2-(4-alkylphenyl)-propionic acid
JPS50131940A (en) * 1974-04-09 1975-10-18
JPS5336456B2 (en) * 1974-04-09 1978-10-03
DE2533397A1 (en) * 1974-07-29 1976-02-12 Nisshin Flour Milling Co PROCESS FOR THE PREPARATION OF 2-ARYLPROPIONIC ACIDS
JPS5318534A (en) * 1976-08-04 1978-02-20 Ota Pharma Production of 22*4** isobutylphenyl* propionic acid
JPS5318535A (en) * 1976-08-04 1978-02-20 Ota Pharma Production of 22*4** isobutylphenyl* propionic acid
JPS5531133B2 (en) * 1976-08-04 1980-08-15
JPS5531132B2 (en) * 1976-08-04 1980-08-15
EP0226566A1 (en) * 1985-11-25 1987-06-24 Monsanto Company Oxidation of 2-arylpropanals
AU589469B2 (en) * 1985-11-25 1989-10-12 Monsanto Company Oxidation of 2-arylpropanals
EP0545891A2 (en) * 1986-04-07 1993-06-09 Sumitomo Chemical Company, Limited Aldehyde compounds and derivatives thereof useful as intermediates in the preparation of insectical ether compounds
EP0545891A3 (en) * 1986-04-07 1993-06-23 Sumitomo Chemical Company, Limited Aldehyde compounds and derivatives thereof useful as intermediates in the preparation of insectical ether compounds
US5260477A (en) * 1988-12-21 1993-11-09 Nippon Petrochemicals Co., Ltd. Method for preparing alpha-(4-isobutylphenyl)propionic acid or its precursor
US5273895A (en) * 1992-10-26 1993-12-28 Sepracor, Inc. Enantioselective production of chiral carboxylic acids
US6096920A (en) * 1997-01-08 2000-08-01 Albemarle Corporation Preparation of carboxylic compounds and their derivatives
WO1999008989A1 (en) * 1997-08-20 1999-02-25 First Chemical Corporation Processes for preparing hydrocinnamic acid
US5939581A (en) * 1997-08-20 1999-08-17 First Chemical Corporation Processes for preparing hydrocinnamic acid

Also Published As

Publication number Publication date
FI49414B (en) 1975-02-28
SE349795B (en) 1972-10-09
FI49414C (en) 1975-06-10
NL6715993A (en) 1968-05-27
CH483386A (en) 1969-12-31
AT281002B (en) 1970-05-11
ES347566A1 (en) 1969-02-01
NO131169B (en) 1975-01-06
NO131169C (en) 1975-04-16

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