Hydrochloric Acid → 4-Benzyloxy-1-butanol

While a suspension containing 2.5 g of 60% sodium hydride was in 50 ml of tetrahydrofuran was allowed to stand at room temperature, 5.7 g of 1,4-butanediol was slowly added dropwise thereto. Then, a solution containing 7.5 ml of benzyl bromide in 20 ml of tetrahydrofuran was added dropwise to the reaction mixture at room temperature, followed by stirring at the same temperature for 2 hours. After the addition of a 10% aqueous solution of HCl, the reaction mixture was extracted with diethyl ether. After the organic layer was washed with an aqueous solution of sodium hydrogen carbonate and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using 150 g of silica gel [with an elution solvent comprising hexane-ethyl acetate (4:1)]. Thus, 5.5 g (48% yield) of the title compound was obtained.

1. customto stand at room temperature
2. additionwas added dropwise to the reaction mixture at room temperature
3. extractionthe reaction mixture was extracted with diethyl ether
4. washAfter the organic layer was washed with an aqueous solution of sodium hydrogen carbonate
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-d83ebcba062b4203a4c9b1278b2181ca

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07087624B2