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 (2×) 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) δ2.6 (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). ##STR142##

Provenance & Evidence