Acetic Acid → Ethyl 3-methylpent-4-enoate

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 36.06 g of crotyl alcohol, 162.2 g of triethyl orthoacetate and 2.22 g of propionic acid was slowly heated to 100° C. (1.25 hours), stirred and heated at 100°-115° C. for 1 hour, at 115°-145° C. for 2.5 hours, then at 145°-155° C. for 6 hours. The mixture was cooled in an ice bath and treated with 50 ml of glacial acetic acid and 50 ml of water. The mixture was stirred at room temperature for 45 minutes, diluted with ether, extracted with saturated sodium bicarbonate solution, then with brine and dried (MgSO4). The solvent was evaporated under reduced pressure and the residue was distilled under reduced pressure to give ethyl 3-methyl-4-pentenoate (3A), as a colorless liquid, b.p.: 88°-91° C. (60 Torr.).

Provenance & Evidence