Triethylamine → Oct-2-enyl acetate

Participants

Reaction Steps

A mixture of 33.6 grams of 1-acetoxyocta-2,7-diene (I), 0.30 g RuCl2 (PPh3)3, 1.5 ml triethylamine and 120 ml ethanol was heated in a 300 ml stainless steel autoclave under a hydrogen pressure of 450 psi at 30° C. After three hours the rate of hydrogenation was greatly decreased and the pressure drop corresponded to approximately the theoretical amount (0.2 moles). The reaction was stopped, the catalyst filtered off and the crude product analyzed by GC to give 12.5% I, 63.7% 1-acetoxyoct-2-ene (II), and 23.6% 1-acetoxyoctane (III). This corresponds to a selectivity of 72.8% for the formation of II at a 87.5% conversion of I.

Provenance & Evidence