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

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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.

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