Benzyl Bromide → ((Prop-2-yn-1-yloxy)methyl)benzene

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium bromide (19.34 g, 600 mmol) was added to a solution of benzylbromide (71.3 ml, 600 mmol) and propargyl alcohol (35.5 ml, 600 mmol) in 270 ml of toluene and the mixture was heated to 50° C. A solution of sodium hydroxide (24 g, 600 mmol) in 55 ml of water was then added dropwise over a period of 1 hour and stirring was continued for another 3 hours. The reaction mixture was then cooled to 25° C. and transferred into a separatory funnel. The aqueous layer was removed and the organic layer was washed three times with 150 ml of brine. Residual water was removed by repeated azeotropic distillation using toluene. A pale yellow liquid was obtained. Yield: 81.9 g (93.4 %).

Provenance & Evidence