Hydrochloric Acid → 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

Participants

Reaction Steps

To a solution of compound 2-(2-(2-(ethoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76.2 mmol) in THF (100 mL) was added 6 N HCl (381 mL). The reaction mixture was stirred at rt overnight, and the obtained mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (6.87 g; yield 51.2% over 2 steps) as a white solid. MS: m/z=177.1 (M+1, ESI+).

Provenance & Evidence