C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][Si:14]([CH2:17][CH2:18][CH2:19][CH3:20])([CH3:16])[CH3:15])(=O)=O)=CC=1.[C:22]1([CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=1)[OH:23].[OH-].[K+].Cl>O.C(O)C.CO>[CH2:17]([Si:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][O:23][C:22]1[CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH3:20]The above-obtained 3-(butyldimethylsilyl)propyl p-toluenesulfonate was added dropwise in 45 min. to a mixture of 2.32 g (21.1 mM) of hydroquinone, 1.13 g (17.1 mM) of 85 %-potassium hydroxide, 6 ml of methanol and 30 ml of ethanol under stirring at 65° C., followed by stirring for 0.5 hour and further stirring for 6 hour at 80° C. After the reaction, the reaction mixture was poured into cold water, acidified with hydrochloric acid (pH≈2) and extracted with ethyl acetate, followed by washing with water and drying with anhydrous magnesium sulfate. The magnesium sulfate in the resultant mixture was filtered off and the filtrate was condensed into a solid, followed by purification by silica gel column chromatography (eluent: toluene) to obtain 2.05 g of 4-[3-(butyldimethylsilyl)propoxy]phenol (Yield: 50.6 %).
Loading…
