Decanal → Methyl-3-hydroxydodec-5-enoic acid

Participants

Reaction Conditions

Reaction Steps

6.5 g of zinc, 15.5 g of decanal, 25 ml of trimethoxyborane, and 25 ml of dried THF were put into a 300 ml four-neck round-bottom flask, and 17.5 g of methyl bromoacetate was dripped at 20° C. for two hours in a nitrogen gas stream. After dripping, a resultant thereof was agitated at 20° C. for one hour, and thereafter, 25 ml of saturated ammonia aqueous solution and 25 ml of glycerin were added and agitated for ten minutes. An organic layer was separated and an aqueous solution layer was extracted two times by using diethyl ether. Thereafter, the organic solution was collected and subjected to desolvation. A residue thereof was purified by distillation to obtain a β-hydroxydodecanoic acid methyl ester.

Provenance & Evidence