FR2156222A1 - Decarboxylation of hydroxyarylcarboxylic acids - - by heating in an aprotic polar medium - Google Patents

Decarboxylation of hydroxyarylcarboxylic acids - - by heating in an aprotic polar medium

Info

Publication number
FR2156222A1
FR2156222A1 FR7235869A FR7235869A FR2156222A1 FR 2156222 A1 FR2156222 A1 FR 2156222A1 FR 7235869 A FR7235869 A FR 7235869A FR 7235869 A FR7235869 A FR 7235869A FR 2156222 A1 FR2156222 A1 FR 2156222A1
Authority
FR
France
Prior art keywords
alkyl
heating
cpds
decarboxylation
alkoxy
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.)
Withdrawn
Application number
FR7235869A
Other languages
French (fr)
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.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
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 International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Publication of FR2156222A1 publication Critical patent/FR2156222A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • 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
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms

Landscapes

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

Abstract

Removal of the carboxylic gp. from cpds. having the formula (in which one of R1 and R3 is OH, and the other one is H, OH, alkyl, or alkoxy, R2 and R4 are the same or different and are H, OH, alkyl or alkoxy, or R3 may from with R2 or R4 an opt. alkylated alkylenedioxy, cycloalkylene, cycloalkenylene, or cycloalkadienylene bridge, in this case R4 or R2 respectively is H, alkyl or alkoxy gps. R5 is H or alkyl and n is 0 or 1) with the proviso that is not >3 OH gps. are attached to the ring, by heating (pref. at 80-220 degrees C) in an aprotic medium having a high dielectric constant (25-100 at 25 degrees C) are free of metals or their cpds. This method is esp. suitable for the prodn. of vinylhydroxyaryl cpds. (such as vinylguaiacol) mfr. of aroma substances, perfumes etc.
FR7235869A 1971-10-12 1972-10-10 Decarboxylation of hydroxyarylcarboxylic acids - - by heating in an aprotic polar medium Withdrawn FR2156222A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18845571A 1971-10-12 1971-10-12

Publications (1)

Publication Number Publication Date
FR2156222A1 true FR2156222A1 (en) 1973-05-25

Family

ID=22693229

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7235869A Withdrawn FR2156222A1 (en) 1971-10-12 1972-10-10 Decarboxylation of hydroxyarylcarboxylic acids - - by heating in an aprotic polar medium

Country Status (8)

Country Link
JP (1) JPS4848431A (en)
AU (1) AU4712972A (en)
BE (1) BE789996A (en)
BR (1) BR7207066D0 (en)
DE (1) DE2248525A1 (en)
FR (1) FR2156222A1 (en)
IT (1) IT1050214B (en)
NL (1) NL7213842A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2637923C2 (en) * 1976-08-23 1984-06-07 Maruzen Oil Co., Ltd., Osaka Process for purifying crude vinylphenol
US4316995A (en) 1981-02-05 1982-02-23 International Flavors & Fragrances Inc. Process for preparing vinyl phenol
JP4802343B2 (en) * 2005-02-22 2011-10-26 和歌山県 Method for producing styrene derivative
JP6008201B2 (en) * 2013-05-10 2016-10-19 東レ・ファインケミカル株式会社 Method for producing styrene derivative
JP2022513699A (en) 2018-12-07 2022-02-09 コベストロ・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・アンド・コー・カーゲー A method for producing a hydroxy compound by decarboxylation in the absence of a catalyst.

Also Published As

Publication number Publication date
JPS4848431A (en) 1973-07-09
BR7207066D0 (en) 1973-08-30
IT1050214B (en) 1981-03-10
DE2248525A1 (en) 1973-04-19
AU4712972A (en) 1974-04-04
BE789996A (en) 1973-04-12
NL7213842A (en) 1973-04-16

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