2-Chloroethanol → 1,2-Bis(2-hydroxyethoxy)benzene

Participants

Reaction Steps

Pyrocatechol [3] (55.0 g, 0.50 mol) was added to a solution (500 mol) of sodium hydroxide (50.5 g, 1.26 mol) in ethanol under purging with nitrogen, and the resultant mixture was refluxed under stirring with a mechanical stirrer for 30 minutes. Ethylene chlorohydrin (96.5 g, 1.20 mol) was dropped into the mixture in 1 hour. After refluxing overnight, the reaction was judged to have been completed. Ethanol was distilled off and chloroform (1.5 l) was added to the residue. The chloroform layer was extracted with an aqueous NaOH solution while the removal of an unreacted matter was confirmed by UV spectroscopy (seven times each with 20 ml of the aqueous NaOH solution for 500 ml of the chloroform layer until no change had been observed in the absorption at around 275 nm in the UV spectrum even when the alkaline aqueous layer turned acidic after the completion of the extraction). Chloroform was distilled off under reduced pressure to obtain the compound [4].

Provenance & Evidence