Benzyl Alcohol → HCID 13198832, compound

Participants

Reaction Steps

A solution of 10.8 ml of benzyl alcohol (103 mmol), 3.16 g of tetrabutylammonium bisulfate (58.5 mmol) and 8.63 g of sodium hydroxide (840 mmol) in water (45.6 ml) was added to a solution of 20.0 g of trans-1,4-dibromo-2-butene (94.7 mmol) in methylene chloride (80 ml) at room temperature, and the mixture was stirred for two days. The reaction mixture was diluted with 300 ml of water, followed by extraction with methylene chloride. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=20/1) to obtain 10.9 g of the title compound (yield: 48%).

Provenance & Evidence