GB824852A - A process for the production of perfumed compositions or perfumed materials or articles containing one or more 3-5-ditertiary-butyl-1-acylbenzenes with the odour character of the musk type - Google Patents

A process for the production of perfumed compositions or perfumed materials or articles containing one or more 3-5-ditertiary-butyl-1-acylbenzenes with the odour character of the musk type

Info

Publication number
GB824852A
GB824852A GB36634/56A GB3663456A GB824852A GB 824852 A GB824852 A GB 824852A GB 36634/56 A GB36634/56 A GB 36634/56A GB 3663456 A GB3663456 A GB 3663456A GB 824852 A GB824852 A GB 824852A
Authority
GB
United Kingdom
Prior art keywords
ditertiary butyl
perfumed
butyl
ditertiary
benzene
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
GB36634/56A
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.)
Polak and Schwarz International NV
Original Assignee
Polak and Schwarz International NV
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 Polak and Schwarz International NV filed Critical Polak and Schwarz International NV
Publication of GB824852A publication Critical patent/GB824852A/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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • 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
    • 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
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • 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
    • C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
    • C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • 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
    • C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
    • C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/542—Alkylated benzaldehydes
    • 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

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)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)

Abstract

Perfumed soap is produced by incorporating in a soap one or more 3.5-ditertiary butyl-1-acyl benzenes of general formula <FORM:0824852/III/1> where R is hydrogen, methyl or ethyl, having a musk-like odour. Specifications 733,111, 774,608, 824,851 and U.S.A. Specifications 2,428,691 and 2,635,114 are referred to.ALSO:Compounds, having the odour character of the musk type, and having the general structure <FORM:0824852/IV (b)/1> where R is hydrogen, methyl or ethyl, i.e. 3,5-ditertiary butyl-benzaldehyde, -acetophenone, or -propiophenone may be produced by (i) direct oxidation of a 3,5-ditertiary butyl-1-alkyl benzene; (ii) monohalogenation with subsequent oxidation of a 3,5-ditertiary butyl-1-alkyl benzene; (iii) dihalogenation with subsequent hydrolysis of ditertiary butyl-1-alkyl benzene; (iv) hydrolysis of the condensation product of 3,5-ditertiary butyl benzoic acid chloride and b -dicarbonyl compounds and analogous compounds, e.g. esters of malonic, cyanoacetic or acetoacetic acid; (v) introduction of an acetyl or propionyl group into 1,3-ditertiary butyl benzene; (vi) introduction of a halomethyl group into 1,3-ditertiary butyl benzene and oxidation thereof; (vii) hydrolysis of the condensation product of 3,5-ditertiary butyl benzonitrile and alkyl magnesium halide; (viii) oxidation of 3,5-ditertiary butyl styrene and side chain homologues as in Specification 774,608; (ix) acylation and replacement of one of the tertiary groups of 1,3,5-tritertiary butyl benzene. Detailed examples of the preparation of the compounds are given. Specifications 733,111 and 824,851 also are referred to.ALSO:Perfumed compositions, materials or articles, e.g. perfumes, lotions, powders, soap, are produced by incorporating into said compositions, materials or articles, one or more 3,5-ditertiary butyl - 1 - acyl benzenes of general formula <FORM:0824852/VI/1> where R is hydrogen, methyl or ethyl, with the odour character of the musk type. Specifications 733,111, 774,608 and 824,851 are referred to.
GB36634/56A 1955-12-03 1956-11-30 A process for the production of perfumed compositions or perfumed materials or articles containing one or more 3-5-ditertiary-butyl-1-acylbenzenes with the odour character of the musk type Expired GB824852A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL824852X 1955-12-03

Publications (1)

Publication Number Publication Date
GB824852A true GB824852A (en) 1959-12-09

Family

ID=19841005

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36634/56A Expired GB824852A (en) 1955-12-03 1956-11-30 A process for the production of perfumed compositions or perfumed materials or articles containing one or more 3-5-ditertiary-butyl-1-acylbenzenes with the odour character of the musk type

Country Status (3)

Country Link
DE (1) DE1037623B (en)
FR (1) FR1164638A (en)
GB (1) GB824852A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112552179A (en) * 2020-12-25 2021-03-26 安徽华业香料股份有限公司 Device and production method for synthesizing musk ketone by using propiolactone byproduct

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112552179A (en) * 2020-12-25 2021-03-26 安徽华业香料股份有限公司 Device and production method for synthesizing musk ketone by using propiolactone byproduct

Also Published As

Publication number Publication date
FR1164638A (en) 1958-10-13
DE1037623B (en) 1958-08-28

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