Acetone → (3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one

Participants

Reaction Steps

To a solution of 25 g (R)-3,7-dimethyl-6-octenal [(R)-citronellal] (chemical purity according to gas chromatography 98.3-98.5%; enantiomeric purity 97-97.6% ee) in 70 ml acetone and 170 ml of water there was added 9.8 g of barium hydroxyde-octahydrate and the mixture was stirred under argon a 68°-69° C. during 4.25 hours. Thereafter, the reaction mixture was cooled to room temperature and extracted two times with 500 ml of n-hexane. The organic phases were combined, washed with 100 ml of water and with 50 ml of 5% aqueous acetic acid, dried over sodium sulfate and concentrated. The so obtained (3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one was 92% chemically pure according to gas chromatography.

Provenance & Evidence