Benzyl Alcohol → HCID 13198832, compound

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%).

1. extractionfollowed by extraction with methylene chloride
2. washThen, the organic layer was washed with water and brine
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationAfter filtration
5. customthe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=20/1)

ORD record

ord-3b365eb04f634e8fa915878aa038b785

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158790B2