Benzyl Chloride → 5-Benzyloxy-2-chloro-nitrobenzene

Participants

Reaction Steps

2.0 g of 4-chloro-3-nitrophenol was dissolved in 15 ml of N,N-dimethylformamide. Thereto was added 490 mg of sodium hydride (purity: 60%) in 10 minutes at 5°-10° C. Then, 1.53 g of benzyl chloride was added dropwise in 10 minutes. Stirring was conducted for 1 hour at 70° C. The reaction mixture was introduced into a mixture of 50 ml of ice water and 50 ml of ethyl acetate. The resulting organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was washed with n-hexane and then mixed with a mixture of diisopropyl ether and n-hexane. The resulting crystal was collected by filtration to obtain 1.8 g (yield: 59.4%) of 4-benzyloxy-2-nitro-chlorobenzene having a melting point of 50°-50.5° C.

Provenance & Evidence