Hydrochloric Acid → HCID 23282419, compound

Participants

Reaction Conditions

Reaction Steps

In a reaction vessel containing 10 ml of N,N-dimethylformamide and 0.088 g of 60% sodium hydride (in oil) was put 0.070 g of methanol under ice cooling, and the mixture was stirred until the evolution of hydrogen gas ceased, to which 0.40 g of 4-(3,3-dichloro-2-propenyloxy)butanol was added. After stirring at 50° C. for 3 hours, the reaction mixture was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.20 g of 4-(3-chloro-2-propynyloxy)butanol (yield, 62%), nD24.6 1.4720.

Provenance & Evidence