Acetic Acid → Butanal, 4-(acetyloxy)-2-methylene-

Participants

Reaction Steps

A solution of 1,4-diacetoxy-2-butene (170 g.) and hydridocarbonyltris(triphenylphosphine) rhodium (I) (0.5 g.) in benzene (340 g.) was heated in a bomb at 75° C. under 2000 psig of a synthesis gas (50% by volume H2 and 50% by volume CO gas). After a few hours, the bomb was cooled and vented and the benzene was removed from the reaction product by distillation. The resulting crude 1,4-diacetoxy-2-formylbutane was then heated to 120°-130° C. in a distillation apparatus under a vacuum of 5 mm Hg. and a distillate (190.3 g. b.p. 60°-80° C.) was collected. The distillate on redistillation gave acetic acid, 2-formyl-4-acetoxybutene (127.1 g., 90.3% yield, b.p. 77°-79° C./ 6 mm Hg) and 1,4-diacetoxy-2-formyl butane (12.5 g., 6.2% yield, b.p. 110°-113° C./ 1 mm Hg.

Provenance & Evidence