4-Nitrophenol → HCID 13839927, compound

Participants

Reaction Steps

A mixture of 139.1 g. (1 mol) 4-nitrophenol, 1 liter butan-2-one and 207.3 (1.5 mol) pulverized, anhydrous potassium carbonate is stirred for 2 hours at reflux temperature, then 292.5 g. (1.5 mol) ethyl 2-bromo-2-methylpropionate are added thereto and the reaction mixture maintained at reflux temperature for a further 92 hours. After the addition of a further 69.1 g. (0.5 mol) potassium carbonate and 97.5 g. (0.5 mol) ethyl 2-bromo-2-methyl-propionate, the reaction mixture is stirred for a further 20 hours at reflux temperature. The reaction mixture is then filtered with suction and the filtrate is evaporated in a vacuum (for the removal of excess ethyl ester, finally at a high vacuum). The residue is taken up in diethyl ether, filtered and the ethereal phase now extracted several times with 1 N aqueous sodium hydroxide solution. After washing until neutral and drying, it is evaporated, 153 g. (60% of theory) of an oily crude product being obtained. After distillation at 155.5°-156° C./0.05 mm.Hg., there is obtained a yield of 46% of theory of pure ethyl 2-methyl-2-(4-nitrophenoxy)-propionate in the form of a yellow oil with a refractive index of nD20 =1.5288.

Provenance & Evidence