Acetaldehyde → 1-Chloroethyl-2,2-dimethyl-3-(phenylmethoxy)propanoate

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Reaction Steps

Following the general procedure for the synthesis of 1-chloroalkyl carboxylic esters of Description 21, 3.7 g (16.5 mmol) of 2,2-dimethyl-3-(phenylmethoxy)propanoyl chloride (26c) was reacted with 1.4 mL (1.1 g, 25 mmol) of acetaldehyde in 70 mL of anhydrous dichloromethane (DCM) in the presence of 0.25 g (1.8 mmol) of zinc chloride (ZnCl2). After work-up and isolation, the product was further purified by silica gel column chromatography using methyl tert-butyl ether (MTBE) and n-heptane (Hptn) mixtures as eluent (MTBE/Hptn=1:9) to provide 0.21 g (5% yield) of the title compound (26) as a yellow oil. Rf=0.24 (MTBE/Hptn=1:9). 1H NMR (400 MHz, CDCl3): δ=1.17 (s, 6H), 1.44 (d, J=5.6 Hz, 3H), 3.54 (s, 2H), 4.50 (s, 2H), 6.87 (q, J=5.6 Hz, 1H), 7.26-7.33 (m, 5H) ppm. The analytical data was consistent with the proposed structure.

Provenance & Evidence