[OH:1][C:2]1[CH:3]=C2[C:9](=[CH:10][CH:11]=1)C=C(C(OCC)=O)C=C2.[OH:17]C1C=C2C(=CC=1)C=C(C(O)=O)C=C2.[I-].[C:32](=[O:35])([O-])[O-:33].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:9][C:10]([CH2:11][C:2]([CH2:3][C:32]([OH:33])=[O:35])=[O:1])=[O:17]
A solution of ethyl 6-hydroxyl-2-naphthate (49, 89 mg, 0.42 mmole) (6-hydroxy-2-naphthoic acid was obtained from TCI America and converted to the ester using standard esterification methods) and iodide (2, 177 mg, 0.42 mmole) in dimethylforamide (1 ml) was stirred with potassium carbonate (174 mg) for 14 hours. The reaction mixture was worked up with water (30 ml) and ethyl acetate (100 ml). The organic layer was washed with brine (30 ml), dried over sodium sulfate, filtered and concentrated. The crude product was purified on a silica gel column (hexane ethyl acetate, 4:1) to provide the triacetate of 3 (120 mg, 55%).
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