[Na].[CH3:2][O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Br[CH2:14][CH2:15][Cl:16]>C(O)C>[CH3:2][O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][CH2:15][Cl:16])=[CH:7][CH:6]=1To 35 mL of ethanol was added sodium pellets (2.27gm, 98.6 mmol). After all the sodium had disappeared methyl-4-hydroxybenzoate (15 gm, 98 mmol) was added in one portion at room temperature. The reaction mixture was then heated to 60° C. and treated dropwise with 1-bromo-2-chloroethane (10.2 gm, 123 mmol) in 15 mL of ethanol. The reaction was stirred for 16 hrs then cooled to room temperature and concentrated. The residue was taken up in ethyl acetate and washed with water, 2N NaOH, and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using 1:10 Ethyl acetate:Hexanes to 1:6 Ethyl acetate:Hexanes as the gradient eluant to yield 11.9 gm of the title compound.
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