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

Temperature

50 °C

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 %).

1. temperatureThe reaction mixture was then cooled to 25° C.
2. customtransferred into a separatory funnel
3. customThe aqueous layer was removed
4. washthe organic layer was washed three times with 150 ml of brine
5. customResidual water was removed
6. distillationdistillation
7. customA pale yellow liquid was obtained

ORD record

ord-4bd27bcd43134be8bb64bdb2444da58d

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589091B2