Water → 1-Bromo-4-(2-propoxyethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

p-Bromophenoxyethanol (2067 g, 9.5227 mol), bromopropane (2342 g, 19.05 mol) and tetrabuthylammonium hydrogensulfate (162 g, 0.476 mol) were dissolved in 10.3 L of dimethyl sulfoxide. A 50 W/W% aqueous sodium hydroxide solution (3.81 kg, 47.625 mol) was dropped slowly. Since heat was generated, the dropping rate and the external temperature were adjusted so that the internal temperature was kept at 40-50° C. After cooling and stirring for 1.5 hours, the mixture was cooled to 20-30° C. and 20.6 L of water was added at that temperature. After addition of 15.5 L of toluene and 4 L of tetrahydrofuran, phase separation was conducted. To the water layer, 5.2 L of toluene 5.2 L and t1.3 L of tetrahydrofuran and extraction was conducted. The organic layers were combined and washed with 20.6 L of water, two 10.3-L portions of 20% brine, two 20.6-L portions of water. After vacuum concentration, the residue was distilled under reduced pressure (135-155° C. /5 mmHg) to yield 2412.8 g (Yield 98%) of 1-p-bromophenoxy-2-propoxyethane as a colorless oily matter.

Provenance & Evidence