GB894638A - A process for the preparation of dihydrojasmone - Google Patents

A process for the preparation of dihydrojasmone

Info

Publication number
GB894638A
GB894638A GB1630059A GB1630059A GB894638A GB 894638 A GB894638 A GB 894638A GB 1630059 A GB1630059 A GB 1630059A GB 1630059 A GB1630059 A GB 1630059A GB 894638 A GB894638 A GB 894638A
Authority
GB
United Kingdom
Prior art keywords
acid
mixture
dihydrojasmone
formula
paraconic
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
GB1630059A
Inventor
Jayramdas Hirabhai Amin
Sasanka Chandra Bhattacharyya
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.)
Council of Scientific and Industrial Research CSIR
Original Assignee
Council of Scientific and Industrial Research CSIR
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 Council of Scientific and Industrial Research CSIR filed Critical Council of Scientific and Industrial Research CSIR
Priority to GB1630059A priority Critical patent/GB894638A/en
Publication of GB894638A publication Critical patent/GB894638A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • 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
    • C07C45/59—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 five-membered rings
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Dihydrojasmone is prepared by subjecting a paraconic acid having the formula <FORM:0894638/IV (b)/1> to pyrolysis at a dicarboxylation temperature to form a mixture of a lactone of the formula <FORM:0894638/IV (b)/2> and an unsaturated acid of the formula <FORM:0894638/IV (b)/3> and cyclodehydrating the mixture by heating with a cyclodehydrating agent containing phosphoric acid thereby obtaining dihydrojasmone. In the example, the paraconic acid is heated with KHSO4 at 250 DEG C.-270 DEG C., the resulting mixture of lactone and unsaturated acid is recovered by vacuum distillation and the mixture then converted into dihydrojasmone by heating with a mixture of phosphoric acid and P2O5 at 100 DEG C., treating the reacted mixture with ice and extracting with petroleum ether. The paraconic acid is obtained by reacting octan-2-one with a di-alkyl ester of succinic acid, e.g. the diethyl ester, in the presence of potassium tert.-butoxide, yielding a half-ester of the general formula <FORM:0894638/IV (b)/4> which is converted into the desired paraconic acid by refluxing with an aqueous solution of hydrobromic and acetic acids.
GB1630059A 1959-05-12 1959-05-12 A process for the preparation of dihydrojasmone Expired GB894638A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1630059A GB894638A (en) 1959-05-12 1959-05-12 A process for the preparation of dihydrojasmone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1630059A GB894638A (en) 1959-05-12 1959-05-12 A process for the preparation of dihydrojasmone

Publications (1)

Publication Number Publication Date
GB894638A true GB894638A (en) 1962-04-26

Family

ID=10074831

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1630059A Expired GB894638A (en) 1959-05-12 1959-05-12 A process for the preparation of dihydrojasmone

Country Status (1)

Country Link
GB (1) GB894638A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304942A (en) * 1980-05-21 1981-12-08 Scm Corporation Producing substituted 2-cyclopentenones
US5136100A (en) * 1989-01-13 1992-08-04 Huls Aktiengesellschaft Process for producing 3-methyl-2-pentyl-cyclopent-2-en-1-one

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304942A (en) * 1980-05-21 1981-12-08 Scm Corporation Producing substituted 2-cyclopentenones
US5136100A (en) * 1989-01-13 1992-08-04 Huls Aktiengesellschaft Process for producing 3-methyl-2-pentyl-cyclopent-2-en-1-one

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