Benzaldehyde → {3-[2-(3,4-Dimethoxyphenyl)ethyl]-2-phenyl-1,3-oxazolidin-5-yl}methanol

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Reaction Steps

A solution of 3 (195 g, 0.76 mol), benzoic acid (3.0 g), benzaldehyde (270 ml), C6H6 (180 ml) was heated to reflux while collecting the H2O in a Dean-Stark trap. After 21/2 hours, 13 ml of H2O was collected and the solution cooled, washed with saturated Na2CO3. The aqueous layer was washed with CHCl3 (2X) and the combined extracts dried, filtered and concentrated to dryness to yield 232 g of 5 which contains 26 mol % benzaldehyde. This corresponds to 209 g of 5; 'H NMR (CDCl3) δ 2.6 (6H, m), 3.4 (2H, m), 3.75 (7H, d, m), 4.3 (1H, m), 4.8 (1H, d), 6.7 (3H, m), 7.4 (5H, bs). ##STR150##

Provenance & Evidence