GB785086A - Novel unsaturated ketones and a process for the manufacture thereof - Google Patents
Novel unsaturated ketones and a process for the manufacture thereofInfo
- 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
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.
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)
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) |
-
1955
- 1955-09-13 GB GB26183/55A patent/GB785086A/en not_active Expired
Cited By (6)
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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