Hydrochloric Acid → 2,4-Dimethylresorcinol

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To a solution of compound 8 (0.90 g, 5.9 mmol) and NaBH3CN (1.1 g, 17.7 mmol) in THF (36 mL) was slowly added 1 M HCl (17.7 mL) to keep pH of the mixture at 3. The mixture was stirred at room temperature for 3 h. Water (50 mL) was added, and then the mixture was extracted with diethyl ether (50 mL×3). The combined organic layers were dried over Na2SO4 and then evaporated. The obtained white powder (0.58 g, 70%) was used to next step without further purification. 1H-NMR (CDCl3, 400 MHz): δ6.85 (1H, d, J=8.1 Hz), 6.37 (1H, d, J=8.1 Hz), 2.22 (3H, s), 2.19 (3H, s). 13C-NMR (CDCl3, 100 MHz) δ152.8, 127.6, 115.1, 109.9, 107.0, 15.5, 8.2.

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