Hydrochloric Acid → (4-Bromo-3-methylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

10.55 g of methyl 4-bromo-3-methylbenzoate was dissolved in 110 mL of tetrahydrofuran, to which 1.31 g of lithium aluminium hydride was added dropwise in small portions at −30 to −20° C., and this mixture was stirred for 15 minutes at −20° C. Then a mixed solution of methanol and water (4:1) was added dropwise to the reaction mixture, and this mixture was stirred for 30 minutes at room temperature. The reaction mixture, to which water was added, was adjusted to pH 7 with 6M hydrochloric acid followed by addition of ethyl acetate, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 9.20 g of (4-bromo-3-methylphenyl)methanol as brown oil.

Provenance & Evidence