GB394197A - Improved processes for the production of perfumes - Google Patents

Improved processes for the production of perfumes

Info

Publication number
GB394197A
GB394197A GB27933/32A GB2793332A GB394197A GB 394197 A GB394197 A GB 394197A GB 27933/32 A GB27933/32 A GB 27933/32A GB 2793332 A GB2793332 A GB 2793332A GB 394197 A GB394197 A GB 394197A
Authority
GB
United Kingdom
Prior art keywords
aldehyde
trimethylcycloheptene
acetone
dimethylcycloheptene
sodium amide
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
GB27933/32A
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.)
M Naef & Cie SA
Original Assignee
M Naef & Cie SA
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 M Naef & Cie SA filed Critical M Naef & Cie SA
Publication of GB394197A publication Critical patent/GB394197A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

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

Abstract

Methyl derivatives of cycloheptene or cyclooctene aldehydes are condensed with acetone, acetaldehyde or their homologues, water being eliminated. Under mild conditions, a condensation product of the aldol type may first be formed and this then converted into the final product. The products are useful as perfumes. The unsaturated aldehydes are prepared by the process described in Specification 392,062. Examples are given of the condensation of (1) 1 : 1 : 7-trimethylcycloheptene - 2 - aldehyde - 3, 1 : 1 : 6-trimethylcycloheptene - 2 - aldehyde - 3, 1 : 1 : 4-trimethylcycloheptene - 2 - aldehyde - 3, 1 : 1 : 6-trimethylcycloheptene-3-aldehyde-4 and 1 : 1-dimethylcyclo-octene-2-aldehyde-3 with acetone, by treatment in the cold with sodium amide or methylate; 1 : 1-dimethylcycloheptene-2-aldehyde-3 is similarly condensed with methylethyl ketone; (2) 1 : 1 : 7-trimethylcycloheptene-2-aldehyde-3 with methylethyl ketone in the presence of dry hydrochloric acid; (3) 1 : 1 -dimethylcycloheptene-2-aldehyde-3 with acetone by passage under reduced pressure over heated alumina; (4) 1 : 1 : 7-trimethylcycloheptene-2-aldehyde-3 with acetone, first by treatment with sodium amide while cooling with ice and then by heating the product with potassium bisulphate or naphthalene-b -sulphonic acid, or by passing its vapour under reduced pressure over active carbon or alumina; (5) 1 : 1 : 6-trimethylcycloheptene-2-aldehyde-3 with acetaldehyde in the presence of sodium methylate; (6) 1 : 1-dimethylcycloheptene-2-aldehyde - 3 with propionaldehyde in the presence of sodium amide.
GB27933/32A 1931-10-30 1932-10-07 Improved processes for the production of perfumes Expired GB394197A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH394197X 1931-10-30

Publications (1)

Publication Number Publication Date
GB394197A true GB394197A (en) 1933-06-22

Family

ID=4514028

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27933/32A Expired GB394197A (en) 1931-10-30 1932-10-07 Improved processes for the production of perfumes

Country Status (1)

Country Link
GB (1) GB394197A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2519327A (en) * 1947-01-13 1950-08-15 Fmc Corp Condensation of beta-(4-methyl-delta3-cyclohexenyl)-butyraldehyde with aldehydes andketones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2519327A (en) * 1947-01-13 1950-08-15 Fmc Corp Condensation of beta-(4-methyl-delta3-cyclohexenyl)-butyraldehyde with aldehydes andketones

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