Ethanone, 1-[4-(1,1-dimethylethyl)phenyl]-, oxime → 4-[2-[(E)-1-(4-tert-butylphenyl)ethylideneamino]oxyethoxy]-3-chlorobenzoic acid

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Reaction Steps

The title compound was prepared as white solid (0.334 g, 53%) from 4-(2-bromo-ethoxy)-3-chloro-benzoic acid methyl ester and 1-(4-tert-butyl-phenyl)-ethanone oxime using a procedure similar to that of step 1 of example 6. mp=167.1-168.8° C.; mass spectrum (+APCI, M+H) m/z 390. 1H NMR (400 MHz, DMSO-d6); δ 12.95 (bs, 1H), 7.89 (d, 1H), 7.84 (dd, 1H), 7.57 (d, 2H), 7.39 (d, 2H), 7.29 (d, 1H), 4.45 (m, 4H), 2.13 (s, 3H), 1.29 (s, 9H). Elemental analysis: Calcd. for C21H24ClNO4: C, 64.69; H, 6.20; N, 3.59, Found: C, 64.50; H, 6.28; N, 3.57.

Provenance & Evidence