[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:20]([CH3:22])[CH3:21].Cl>CN(C=O)C>[CH3:21][CH:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)[CH3:22]Methyl (4-hydroxyphenyl)acetate (1.0 g, 1.0 eq), Cs2CO3 (2.15 g, 1.1 eq) and 2-bromopropane (0.565 mL. 1.0 eq) were combined in 100 ml DMF at room temperature. The mixture was stirred overnight. The suspension was poured into 50 mL 1 N HCl and extracted with ethyl acetate. The organic phase was separated and washed with water followed by sodium bicarbonate. The organic phase was dried over sodium sulfate and the solvent was evaporated to give an oil. The resulting oil was chromatographed on silica gel using hexanes and ethyl acetate (95:5) to give methyl (4-(1-methylethoxy)phenyl)acetate.
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