GB785086A - Novel unsaturated ketones and a process for the manufacture thereof - Google Patents

Novel unsaturated ketones and a process for the manufacture thereof

Info

Publication number
GB785086A
GB785086A GB26183/55A GB2618355A GB785086A GB 785086 A GB785086 A GB 785086A GB 26183/55 A GB26183/55 A GB 26183/55A GB 2618355 A GB2618355 A GB 2618355A GB 785086 A GB785086 A GB 785086A
Authority
GB
United Kingdom
Prior art keywords
methyl
reacted
ester
aceto
alkali metal
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
GB26183/55A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB785086A publication Critical patent/GB785086A/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
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • 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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom

Landscapes

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

Abstract

The invention comprises unsaturated ketones having the general formula <FORM:0785086/IV (a)/1> wherein R1 represents a C2-5 alkyl radical or a phenyl radical and R2 represents methyl or R1 and R2 together represent the pentamethylene radical. They are obtainable by reacting a vinyl alcohol <FORM:0785086/IV (a)/2> wherein R1 and R2 are as defined above, with a hydrogen halide or phosphorus halide, condensing the resulting substituted primary allyl halide with an alkali metal salt of an acetoacetic ester and submitting the resulting substituted aceto-acetic ester to a ketonic hydrolysis. The vinyl alcohols are preferably reacted with concentrated aqueous hydrogen chloride or bromide or with phosphorus tribromide. The condensation step may be effected with the alkali metal salt of the aceto-acetic ester in an inert solvent or with the ester itself and an alkali metal alcoholate. In examples: (1) 3-methyl - penten - (1) - ol - (3) is reacted with aqueous HCl, the resulting 1-chloro-3-methylpentene-2 is isolated and reacted with a mixture of ethyl aceto-acetate and sodium methylate yielding 3 - carbethoxy - 6 - methyl - octen - (5) - one-2 which is treated with KOH in aqueous ethanol to form the potassium salt of the corresponding ketonic acid and then with concentrated hydrochloric acid giving 6-methyl-octen-(5)-one-2; the ethyl aceto-acetate may be replaced by the methyl ester; (2) 1-vinyl-cyclohexanol-(1) is reacted as in (1) to give 5-cyclohexylidene-pentanone-2 and (3) in the same manner, 3:5 - dimethyl - hexen - 1 - ol - (3) is used to form 6:8-dimethyl-noren-(5)-one-(2). Another specified alcohol is 3-phenyl-buten-(1)-ol-(3). The unsaturated ketones have the properties of perfumes. Specification 735,828 is referred to.
GB26183/55A 1954-09-13 1955-09-13 Novel unsaturated ketones and a process for the manufacture thereof Expired GB785086A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US785086XA 1954-09-13 1954-09-13

Publications (1)

Publication Number Publication Date
GB785086A true GB785086A (en) 1957-10-23

Family

ID=22144463

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26183/55A Expired GB785086A (en) 1954-09-13 1955-09-13 Novel unsaturated ketones and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB785086A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014056847A1 (en) * 2012-10-08 2014-04-17 Dsm Ip Assets B.V. Flavor and fragrance formulation (ii)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014056847A1 (en) * 2012-10-08 2014-04-17 Dsm Ip Assets B.V. Flavor and fragrance formulation (ii)
CN104704096A (en) * 2012-10-08 2015-06-10 帝斯曼知识产权资产管理有限公司 Flavor and fragrance formulation (ii)
US20150245985A1 (en) * 2012-10-08 2015-09-03 Dsm Ip Assets B.V. Flavor and fragrance formulation (ii)
JP2016501918A (en) * 2012-10-08 2016-01-21 ディーエスエム アイピー アセッツ ビー．ブイ． Flavored Aroma Formula (II)
US9468594B2 (en) 2012-10-08 2016-10-18 Dsm Ip Assets B.V. Flavor and fragrance formulation (II)
CN104704096B (en) * 2012-10-08 2020-09-29 帝斯曼知识产权资产管理有限公司 Flavor and fragrance formulation (II)

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