Benzenesulfonyl chloride → Benzenesulfonic acid 3-benzyloxy-5-methylphenyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 3-benzyloxy-5-methylphenol (400 mg, 2.0 mmol), as prepared in step a of Example 3, in methylene chloride (10 mL) at 0° C. was treated with N,N-diisopropylethylamine (0.4 mL) and benzenesulfonyl chloride (354 mg, 2.0 mmol). The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 2 h. The reaction mixture was diluted with methylene chloride (200 mL) and water (50 mL). The organic extract was washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a colorless liquid (675 mg, 95%). 1H-NMR(300 MHz, CDCl3) δ 2.24 (s, 3H), 4.91 (s, 2H), 6.40 (t, 1H), 6.43 (s, 1H), 6.68 (s, 1H), 7.36 (m, 5H), 7.52 (t, 2H), 7.64 (d, 1H), 7.83 (t, 2H).

Provenance & Evidence