Acetone → 1,3-Propanediol, 2-(4-pentenyl)-

Participants

Reaction Steps

A suspension of 13.8 g of lithium aluminium hydride in 500 ml of tetrahydrofuran was treated dropwise under nitrogen at 0°-5° C. within 1 hour with a solution of 33.2 g of diethyl (4-pentenyl)malonate in 125 ml of tetrahydrofuran. The mixture was stirred overnight at room temperature and then heated to boiling for 3 hours. After cooling there were cautiously added dropwise to the reaction mixture firstly 25 ml of acetone and then 25 ml of saturated sodium hydrogen carbonate solution. The resulting slurry was suction filtered and the residue on the suction filter was washed four times with tetrahydrofuran. Concentration of the filtrate gave 17.8 g of 2-(4-pentenyl)-1,3-propanediol (purity 89%) as a yellow liquid.

Provenance & Evidence