4-tert-Butyl-3-methoxybenzoic acid → 1206775-43-0

Participants

Reaction Steps

step a—To a solution of 4-tert-butyl-3-methoxybenzoic acid (3.00 g, 14.40 mmol, CASRN 79822-46-1) in THF (60 mL) cooled to 5° C. was added dropwise a solution of BH3-Me2S (2.0M in THF, 16.60 mL, 33.10 mmol). The reaction was allowed to stir for 24 h at RT then cooled to −50° C. and quenched by dropwise addition of MeOH (20 mL). The reaction mixture was warmed to RT and concentrated in vacuo. The residue was taken up in MeOH (3×20 mL) and concentrated in vacuo. The final residue partitioned between EtOAc and sat'd. aq. NaHCO3. The organic layer was washed with water, brine, dried (MgSO4), filtered and concentrated to afford 2.64 g (95%) of (4-tert-Butyl-3-methoxy-phenyl)-methanol (345) as a colorless oil.

Provenance & Evidence