Diisobutylaluminum hydride → 3-Hexadecyloxy-2-methylenepropan-1-ol

Participants

Reaction Steps

To a solution of 21 g of ethyl 2-[(hexadecyloxy)methyl]-2-propenoate in 400 ml of ether cooled to 0° C. under an inert atmosphere is added 2.25 ml of 1.2M DIBAL in hexanes over 30 minutes. The reaction is stirred at ambient temperature for 2 hours then cooled to 0° C. while 20 ml of saturated sodium sulfate is added dropwise. After filtering, the cake is washed with ether. The combined ether washings are dried and the solvent removed. The residue is crystallized from methyl alcohol:water to give 25.8 g of the desired product as a colorless solid.

Provenance & Evidence