Benzene → Butanal, 4-(acetyloxy)-2-methylene-

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,4-diacetoxy-2-butene (170 g.), triphenylphosphite (0.51 g.), 5% rhodium on charcoal (1.12 g.) and benzene (340 g.) was loaded into a 1 liter stainless steel autoclave and heated with stirring to 85° C. The autoclave was then pressured to 2000 psig with synthesis gas. When gas uptake had ceased (approximately 3 hours), the autoclave was cooled to room temperature and vented. The reaction mixture was filtered and heated under vacuum until all the benzene had been removed. After the addition of p-toluenesulphonic acid (0.5 g.), the reaction product was heated in an oil bath at 105°-110° C. under a vacuum of 5 mm Hg. and the distillate so produced was collected and then fractionally distilled to give 2-formyl-4-acetoxybutene (126.3 g., 90% yield, b.p. 67°-72° C./ 6 mm Hg.).

Provenance & Evidence