Reaction #84018

Reaction equation

decanal

trimethoxyborane

ammonia aqueous

methyl bromoacetate

→

β-hydroxydodecanoic acid methyl ester

Solvents

THF

glycerin

Conditions

Workup

1. 1
   workup.STIRRINGagitated for ten minutes
2. 2
   OtherAn organic layer was separated
3. 3
   Extractionan aqueous solution layer was extracted two times
4. 4
   OtherThereafter, the organic solution was collected
5. 5
   workup.DISTILLATIONA residue thereof was purified by distillation

Procedure

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.

Source