2,5-Dichlorophenol → HCID 88743094, compound

Participants

Reaction Steps

To a three-necked, 1000 ml flask provided with a mechanical stirrer and a reflux condenser was added 130.4 grams (0.8 mole) 2,5-dichlorophenol (prepared as described in step 1) dissolved in 300 ml absolute, i.e., anhydrous, ethanol. To the phenol solution was added, at ambient temperature, 32.4 grams (0.81 mole) sodium hydroxide dissolved in 300 ml absolute ethanol. The resulting mixture was stirred for 30 minutes and then 133.6 grams (0.8 mole) ethyl bromoacetate was added over a period of 15 minutes. The resulting mixture was stirred for about 30 hours at ambient, i.e., about 23° C., temperature. (A white precipitate, believed to be sodium bromide, was apparent after stirring for about 1 hour.) After completion of stirring the mixture was filtered and the filtrate was concentrated on a rotary evaporator at 55° C., 140 mm Hg and a suspended solids containing liquid was obtained. Both the liquid and the solids were taken-up in 200 ml carbon tetrachloride and transferred to a separatory funnel. The mixture was washed twice with 50 ml portions of 1 N sodium hydroxide solution and once with 50 ml of water. After washing, the organic phase was separated, dried over magnesium sulphate, filtered and the filtrate concentrated on a rotary evaporator at 55° C., 140 mm Hg, a reddish-yellow liquid being obtained. The liquid was taken up in 150 ml of carbon tetrachloride, treated with 2 grams activated charcoal, filtered and the filtrate was concentrated on a rotary evaporator at 55° C., 140 mm Hg. 190 grams of a light yellow liquid corresponding to a 92 percent yield of ethyl-2,5-dichlorophenoxy acetate was thus obtained.

Provenance & Evidence