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

Participants

Reaction Steps

A 3 l, three-necked, round bottomed flask fitted with a mechanical stirrer was charged with 6 g of Raney-Nickel, 500 ml of ethyl acetate and 127 g of (3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one. The flask was purged with hydrogen and stirring was initiated at room temperature. Hydrogenation was carried out under a pressure of 2 bar. After 2 hours the reaction was stopped. The total hydrogen uptake was about 14.2 l. The reaction mixture was filtered and concentrated to give a pale yellow oil of (R)-6,10-dimethyl-9-undecene-2-one which was distilled under vacuum using a 40 cm Vigreux distillation column, and the following fractions were collected:

Provenance & Evidence