Benzyl Bromide → HCID 68583368, compound

Participants

Reaction Steps

To a solution of 2-allyl-4-chloro-1-naphthol (20.0 g, 0.091 mol) in N,N-dimethylformamide (700 mL) was added sodium hydride (60 wt. %, 4.39 g, 0.11 mol) and the reaction mixture was allowed to stir at room temperature for 30 min. Benzyl bromide (18.8 g, 0.11 mol) was then added and the reaction mixture was allowed to stir at room temperature for 2 h. The solvent was removed in vacuo to provide a crude oil. The residue was re-dissolved in ethyl acetate (500 mL) and the organic layer was washed with water (2×250 mL), saturated aqueous sodium chloride (250 mL), dried (sodium sulfate) and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, dichloromethane:hexanes 1:4) provided 23.0 g (82%) of 2-allyl-1-(benzyloxy)4-chloronaphthalene as a light brown oil. Treatment of the benzyl ether with AD-mix-α (104.3 g) generally according to the procedure described for Intermediate 2 afforded 24.0 g (94%) of (±)-3-[1-(benzyloxy)-4-chloro-2-naphthyl]propane-1,2-diol as a white solid. mp 69-71° C.; Anal. calcd. for C20H19ClO: C, 70.07; H, 5.59. Found: C, 68.01; H, 5.47.

Provenance & Evidence