Benzyl Bromide → HCID 86747691, compound

Participants

Reaction Steps

4-sulfonaphthalic anhydride (Orlex Chemical Corp., Fairlawn, N.J.) or the corresponding potassium salt (Aldrich Chemical Co., Milwaukee, Wis.) is fused with molten potassium hydroxide, cooled, and acidified. The resulting 4-hydroxynaphthalic anhydride is removed by filtration and treated with one equivalent of potassium carbonate and benzyl bromide to obtain 4-benzyloxy naphthalic anhydride. Lithium tetrahydride aluminate (lithium aluminum hydride) reduction in tetrahydrofuran for 3 h at reflux temperatures gives the 1-8-naphthalenedimethanol. A suspension of the dimethanol (1.3 g, 5.0 mmol) in toluene (15 ml) is treated with a solution of phosphorous bromide (0.7 ml, 0.2 g, 7.5 mmol) in methylene chloride (7.5 ml) during 20-30 minutes and reacted for an hour. The solution is poured into ice-water, diluted with ethyl acetate, partitioned, and the organics are washed with 5% sodium chloride solutions. Drying and evaporation of solvent gives a crystalline residue (1.94 g) which deposits 1,8-dibromomethylene -4-benzyloxynaphthalene (1.3 g, m.p. 59°-60° C.) from hexane solution.

Provenance & Evidence