[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:14]1([CH2:20][CH2:21][CH2:22]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.CN(C=O)C.CCOC(C)=O.O>[C:14]1([CH2:20][CH2:21][CH2:22][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1To a solution of p-hydroxybenzoic acid, methyl ester (2.0 g, 13.2 mmol) in toluene/DMF (2:1) under argon was added NaH (630 mg, 2.0 eq.). After stirring for 15 minutes 3-phenylpropyl bromide (3.0 ml, 1.5 eq.) was added and the mixture refluxed for 4 hours. The solution was diluted with EtOAc and water. The organic layer was washed with H2O, 5% KHSO4 and brine, then dried over anhydrous MgSO4. Concentration in vacuo gave a yellow oil which solidified upon standing. Recrystallization from hexane/EtOAc gave title compound, a cream colored solid, 1.35 g (38%).
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