4-[(4-chloroanilino)methyl]-2-methoxyphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.9 g of 4-(4-chloroanilinomethyl)-2-methoxyphenol, 2.11 g of ethyl 2-bromo-2-methylpropionate 1.5 g of potassium carbonate and 29 ml of methyl isobutyl ketone is refluxed for 24 hours. To the mixture is further added 705 mg of ethyl 2-bromo-2-methylpropionate and the resulting mixture is further refluxed for 3 hours. The insolubles are filtered off and the filtrate is washed with water, dried and concentrated under reduced pressure. The residual oil is purified by column chromatography, using 60 g of silica gel and benzene as a developer, to give 1.1 g of ethyl 2-[4-(4-chloroanilinomethyl)-2-methoxyphenoxy]-2-methylpropionate, mp 73° to 74° C. Infrared absorption spectrum (nujol) 3400, 1735 cm-1. N.M.R.spectrum (CDCl3, δ) ppm 6.45-7.33 (7H, m), 4.25 (2H, q, J=7 Hz), 4.20 (2H, s) 3.79 (3H, s), 1.59 (6H, s), 1.30 (3H, t, J=7 Hz) is refluxed for 24 hours the resulting mixture is further refluxed for 3 hours The insolubles are filtered off the filtrate is washed with water dried concentrated under reduced pressure The residual oil is purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir: