[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[H-].[Na+].Cl[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.[I-].[Na+]>CN(C=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1To a solution of 2-naphthol (26 g) in DMF (300 ml) is added sodium hydride (7.2 g of 60% dispersion). When gas evolution ceases, methyl 4-(chloromethyl)benzoate (32.9 g) and sodium iodide (10 g) are added, and the reaction mixture is stirred at 140° for 3 hr, and at 90° for an additional 18 hr. The mixture is cooled, poured into 2000 ml ice water, and the product extracted with 1:1 ether-hexane. The extracts are dried, filtered, and concentrated, providing methyl 4-(2-naphthyloxymethyl)benzoate as a tan solid (42.8 g, 91%). The ester is reduced with lithium aluminum hydride in THF in the usual fashion, and the resulting benzyl alcohol is converted by Swern oxidation (oxalyl chloride /DMSO) to 4-(2-naphthyloxymethyl)benzaldehyde. By the method of example 1, this is converted to the title compound, obtained as a pale yellow solid, mp. 213°-215° after recrystallization from hexane-ethyl acetate.
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