2-Chloroethanol → 4-(2-Hydroxyethoxy)benzenecarboxylic acid

Participants

Reaction Steps

300 g of potassium hydroxide were dissolved in a mixed solution of 700 ml of ethanol and 100 ml of water. After dissolving 276 g of 4-hydroxybenzoic acid and a catalytic amount of potassium iodide in the solution, 177 g of ethylene chlorohydrin was gradually added to the mixture in a heated state followed by refluxing for about 15 hours. After distilling off ethanol from the reaction mixture obtained, the residue was added to 2 liters of water. After washing the aqueous solution obtained twice with diethyl ether, the solution was acidified by the addition of hydrochloric acid, and the precipitates thus formed were collected by filtration and dried, and recrystallized from ethanol to obtain 298 g (yield 82%) of 4-(2-hydroxyethoxy)benzoic acid.

Provenance & Evidence