Hydroquinone → 4-(tert-Butyldimethylsiloxy)phenol

Participants

Reaction Steps

To a solution of hydroquinone (1.0 g, 0.9 mmol) and tert-butyldimethylsilylchloride (1.4 g, 0.9 mmol) in 5 mL of dry DMF was gradually added imidazole(1.2 g, 1.8 mmol) and the solution was stirred for 1 hour. TLC analysis (silica gel, 20% ethyl acetate/hexane) showed completion of reaction. The solution was poured into 25 mL of water and extracted with 3×25 mL of ether. The combined ether solutions were dried over anhydrous MgSO4. Evaporation of solvent gave an oil which was chromatographed on silica using 20% ethyl acetate/hexane to give the product as a white solid in 70% yield: 1H NMR (CDCl3) δ0.145 (s, 6H), 0.956 (s, 9H), 4.47 (bs, 1H), 6.68 (s, 4H); 13C NMR (CDCl3) δ-4.48, 18.21, 25.74, 115.93, 120.55, 120.81, 149.78.

Provenance & Evidence