Ethanone, 1-[4-(1,1-dimethylethyl)phenyl]-, oxime → 4-[2-[(E)-1-(4-tert-butylphenyl)ethylideneamino]oxyethoxy]-2-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)-2-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=142.7-143.9° C.; mass spectrum (−ESI, M−H) m/z 388. 1H NMR (400 MHz, DMSO-d6); δ 12.97 (bs, 1H), 7.81 (d, 1H), 7.57 (d, 2H), 7.40 (d, 2H), 7.14 (d, 1H), 7.02 (dd, 1H), 4.42 (t, 2H), 4.38 (t, 2H), 2.13 (s, 3H), 1.28 (s, 9H). Elemental analysis: Calcd. for C21H24ClNO4: C, 64.69; H, 6.20; N, 3.59, Found: C, 64.43; H, 6.20; N, 3.42.

Provenance & Evidence