[OH-].[Na+].[CH:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([Br:10])[CH:4]=1.[H][H].Br[CH2:14][C:15]1[C:16]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=1>O.CN(C)C=O.CCCCCC>[Br:10][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([O:23][CH3:24])=[O:22])=[CH:3][CH:4]=1Wash 15.12 gm (0.315 mole) of sodium hydroxide, 50% dispersion in oil, free of oil with hexane and suspend in 250 cc. of N,N-dimethylformamide. Add 54.5 gm. (0.315 mole) of p-bromophenol in portions as hydrogen is evolved. After gas evolution has subsided, add a solution of 68 gm. (0.3 mole) of methyl α-bromo-o-toluate in 50 cc. of N,N-dimethylformamide at a rapid dropwise rate. Stir the mixture for 45 minutes and pour into 3 liters of cold water. Separate the solids by filtration, wash with water and dry to obtain 90 gm. of crude methyl o-(p-bromophenoxymethyl)benzoate which is used in the next step without further purification.
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