Boron tribromide → 5,5-DIMETHYL-5,6,7,8-TETRAHYDRONAPHTHALEN-2-OL

Participants

Reaction Conditions

Reaction Steps

To a methylene chloride (10 ml) solution of 6-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Tetrahedron, 1994, 50, 3297) (2.28 g, 12.0 mmol) was added methylene chloride solution of boron tribromide (1M, 24 mL, 24.0 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hours. The reaction mixture was then quenched with methanol and then the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=⅓ to furnish 2.0 g (96% yield) of the title compound as a white solid.

Provenance & Evidence