Phenol → Diethyl(2-phenoxyethyl)amine

Participants

Reaction Conditions

Reaction Steps

A solution of 108.5 g (0.630 mol; 1.2 eq.) of N-(2-chloroethyl)-N,N-diethylamine hydrochloride in 65 ml of water is added slowly (over about 55 minutes) to a mixture containing 50 g (0.531 mol) of phenol and 46.3 g (1.158 mol; 2.2 eq.) of NaOH in 270 ml of water. The mixture is stirred for 3 hours 30 minutes at 20° C. and then for 45 minutes at 55° C. The phases are separated by settling and the supernatant oil diluted in 100 ml of DCE is washed with (i) 100 ml of 2.5% sodium hydroxide and then (ii) with 100 ml of 5% sodium hydroxide. The product is dried over sodium sulfate and then concentrated. 81.4 g of crude N,N-diethyl-N-(phenoxyethyl)amine are obtained.

Provenance & Evidence