Reaktion #84018

Reaktionsgleichung

decanal

trimethoxyborane

ammonia aqueous

methyl bromoacetate

→

β-hydroxydodecanoic acid methyl ester

Lösungsmittel

THF

glycerin

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle