Water → 3,3-Dimethylhex-5-en-2-one

Participants

Reaction Steps

A mixture of 121 g (1.0 mol) of 3-bromopropene and 103 g (1.2 mol) of 3-methyl-2-butanone is added dropwise during the course of 2 hours to a suspension of 168 g (3.0 mol) of potassium hydroxide powder and 10 g of tetrabutylammonium bromide in 300 ml of toluene with stirring. During this addition, the reaction temperature is kept below 30° C. The reaction mixture is kept at room temperature for a further 2 hours, then mixed with water, and the organic phase is separated. The organic phase is washed twice with water, dried and distilled through a packed column at ambient pressure. 40 g (31.7% of theory) of 4,4-dimethyl-1-hexen-5-one are obtained as a clear liquid of boiling point 151°-154° C.

Provenance & Evidence