[Br-].OC[C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=O)=[CH:6][CH:5]=1.[C:13](=[O:16])([O-])[O-:14].[Cs+].[Cs+].CN([CH:22]=[O:23])C>C(OCC)(=O)C.O.CO>[CH2:8]([O:14][C:13](=[O:16])[C:4]1[CH:12]=[CH:11][C:7]([CH2:22][OH:23])=[CH:6][CH:5]=1)[C:7]1[CH:6]=[CH:5][CH:4]=[CH:12][CH:11]=1
Benzy bromide (7.8 mL, 66 mmol) was added to a suspension of 4-hydroxymethylbenzoic acid (10 g, 66 mmol) and cesium carbonate (11 g, 34 mmol) in mixed solvent (DMF 0.10 L-methanol 30 mL-water 30 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Water (0.50 L) and ethyl acetate (0.50 L) were added to the reaction solution, and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (0.30 L) and water (0.30 L) twice, respectively. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained solid was filtered and dried at 35° C. under reduced pressure to give 13 g of the title reference compound as a white solid. (Yield 81%)
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