GB852935A - Production of alkyl-substituted cyclohexenones - Google Patents

Production of alkyl-substituted cyclohexenones

Info

Publication number
GB852935A
GB852935A GB1314358A GB1314358A GB852935A GB 852935 A GB852935 A GB 852935A GB 1314358 A GB1314358 A GB 1314358A GB 1314358 A GB1314358 A GB 1314358A GB 852935 A GB852935 A GB 852935A
Authority
GB
United Kingdom
Prior art keywords
alkyl
acetyl
cyclohex
methyl
hydrogen atom
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
GB1314358A
Inventor
Richard Norman Lacey
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers 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 Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB1314358A priority Critical patent/GB852935A/en
Publication of GB852935A publication Critical patent/GB852935A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C07C49/798—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring containing rings other than six-membered aromatic 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/603—Unsaturated compounds containing a keto groups being part of a ring of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings

Landscapes

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

Abstract

The invention comprises alkyl-substituted cyclohexenones of the formula : <FORM:0852935/IV(b)/1> wherein R1 represents an alkyl or an aryl group, R2 represents an alkyl or aryl group or a hydrogen atom, R3 represents an alkyl group or a hydrogen atom and R4 represents an alkyl group or a hydrogen atom and R4 represents an alkyl group and a process from the production of an alkyl-substituted cyclohexenone which comprises heating a diketone of the structural formula : <FORM:0852935/IV(b)/2> wherein R1 represents an alkyl group or an aryl group with an alpha-beta unsaturated ketone of the structural formula : <FORM:0852935/IV(b)/3> wherein R2 represents an alkyl or aryl group or a hydrogen atom, R3 represents an alkyl group or a hydrogen atom and R4 represents an alkyl group in the presence as catalyst of an oxide, hydroxide or alkoxide of an alkali metal or an alkaline earth metal. Specified metals from which the catalysts may be derived include sodium, potassium, calcium and magnesium. Diketones specified are acetyl- and benzoylacetones and a -b -unsaturated ketones specified include methyl isopropenyl ketone, methyl vinyl ketone, ethylidene acetone, benzylidene acetone, 2-methylpent-1-en-3-one and 3-ethylbut-3-en-2-one. The products may be hydrolysed to the corresponding alkyl cyclohexenones. Examples relate to the production of 6-acetyl-3:4-dimethyl-cyclohex-2-en-1-one, 6-acetyl-3-methyl-cyclohex-2-en-1-one, 6-acetyl-3-5-dimethyl-cyclohex-2-en-1 -one, 6-acetyl-3-methyl-5-phenyl-cyclohex-2-en-1 -one, 6-acetyl-3-ethyl-4-methylcyclohex-2-en-1-one, 6-acetyl-4-ethyl-3-methyl-cyclohex-2-en-1-one and 6-benzoyl-3-methyl-cyclohex-2-en-1-one.
GB1314358A 1958-04-25 1958-04-25 Production of alkyl-substituted cyclohexenones Expired GB852935A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1314358A GB852935A (en) 1958-04-25 1958-04-25 Production of alkyl-substituted cyclohexenones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1314358A GB852935A (en) 1958-04-25 1958-04-25 Production of alkyl-substituted cyclohexenones

Publications (1)

Publication Number Publication Date
GB852935A true GB852935A (en) 1960-11-02

Family

ID=10017642

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1314358A Expired GB852935A (en) 1958-04-25 1958-04-25 Production of alkyl-substituted cyclohexenones

Country Status (1)

Country Link
GB (1) GB852935A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0941980A1 (en) * 1998-03-12 1999-09-15 Basf Aktiengesellschaft Process for the preparation of 2,5,6-trimethyl-cyclohex-2-en-1-on
CN103535678A (en) * 2012-07-17 2014-01-29 西姆莱斯有限公司 Use of defined cyclohexenones as agents for the superadditive enhancement of an olfactory impression and fragrance and/or flavor material composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0941980A1 (en) * 1998-03-12 1999-09-15 Basf Aktiengesellschaft Process for the preparation of 2,5,6-trimethyl-cyclohex-2-en-1-on
US5994589A (en) * 1998-03-12 1999-11-30 Basf Aktiengesellschaft Process for preparing 2,5,6-trimethyl-2-cyclohexen-1-one
CN103535678A (en) * 2012-07-17 2014-01-29 西姆莱斯有限公司 Use of defined cyclohexenones as agents for the superadditive enhancement of an olfactory impression and fragrance and/or flavor material composition

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