2,3,6-Trimethylcyclohexan-1-one → Dehydrolinalool

HRID 371963

반응식

HRID 371963 반응식
CC1C(C)CCC(C)C1=[O:10].[CH3:11][C:12](=[CH:14][CH2:15][CH:16]=[C:17]([CH3:20])[C:18]#[CH:19])[CH3:13].CC(=CCCC(=C)C#C)C>O>[CH3:11][C:12]([CH3:13])=[CH:14][CH2:15][CH2:16][C:17]([OH:10])([C:18]#[CH:19])[CH3:20]

참가 물질

5

반응물 3

HCID 1425832,3,6-Trimethylcyclohexan-1-oneHCID 110189207-Methyl-3-methyleneoct-6-en-1-yneHCID 536466313,7-Dimethyl-3,6-octadien-1-yne

생성물 1

HCID 62842Dehydrolinalool

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 28 g of 2,3,6-trimethyl-cyclohexanone and 27 g of the isomer mixture consisting of 2,6-dimethyl-oct-2,5-dien-7-yne and 2-methyl-6-methylene-oct-2-en-7-yne, obtained by elimination of water from 2-dehydrolinalool, is added dropwise to a suspension of 35 g of KOH in 200 ml of toluene at 0° C. The reaction mixture is then kept for 6 hours at 0° C, whilst being stirred, after which water is added and the organic phase formed is dried and concentrated. Subsequent fractional distillation gives 12.3 g of unconverted trimethylcyclohexanone and 12 g of a mixture of 2,3,6-trimethyl-1-(3',7'-dimethyl-oct-1'-yn-3',6'-dien-1'-yl)-cyclohexanol and 2,3,6-trimethyl-1-(7'-methyl-3'-methylene-oct-1'-yn-6'-en-1'-yl)-cyclohexanol of boiling point 125°-127° C/0.4 mm Hg as a viscous oil. This corresponds to a yield of 39%, based on ketone converted. Fragrance note: faintly floral, spicy, minty.

출처 및 근거

ORD 기록
ord-40f80c9de7f54eaaa1969fce159f4ab8
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04088681

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