Sodium Bicarbonate → HCID 54409244, compound

Participants

Reaction Steps

To a solution of 1.00 g (8.05 mmol) of orcinol monohydrate and 1.63 g (7.38 mmol) of 2-methoxy-m-toluenesulfonyl chloride in 20 mL of diethyl ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2×30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2SO4) and concentrated to give 2.2 g of an orange syrup. Crystallization from dichloromethane-hexane (two crops) afforded 1.24 g (54%) of the title compound as a light orange powder: 1H-NMR (300 MHz; CDCl3) δ 7.62 (d, 1 H, J=2.0 Hz), 7.40 (m, 1 H), 6.96 (d, 1 H, J=8.5 Hz), 6.52 (m, 2 H), 6.42 (t, 1 H, J=2.1 Hz), 5.13 (s, 1 H), 3.96 (s, 3 H), 2.29 (s, 3 H) and 2.23 (s, 3 H).

Provenance & Evidence