Orcinol → HCID 53957774, compound

Participants

Reaction Steps

To a solution of 2.0 g (16.1 mmol) of orcinol in diethyl ether (100 mL) containing 10 mL of N,N-diisopropylethylamine was added in a slow steady stream 3.05 g (16 mmol) of α-toluenesulfonyl chloride in a solution of 1:1 diethyl ether/dichloromethane (ca. 30 mL). The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was quenched with 10% hydrochloric acid, extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5 to 90:10)) to give 848 mg of the title compound as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 7.37-7.48 (m, 5H), 6.56-6.57 (m, 1H), 6.51-6.52 (m, 1H), 6.43 (t, 1H, J=2 Hz), 5.21 (s, 1H), 4.50 (s, 2H), 2.26 (s, 3H).

Provenance & Evidence