3-Bromophenol → 3-(3,7-Dimethyloctyloxy)bromobenzene

Participants

Reaction Conditions

Reaction Steps

450 ml of ethanol were initially introduced, and Nal (10.5 g; 70 mmol) and KOH (67.3 g; 1.2 mol) were added. A temperature increase from 25 to 40° C. after addition of the KOH was observed. After the mixture had been cooled to room temperate, 3-bromophenol (176.5 g; 1 mol) was added, during which the white suspension became beige. 3,7-Dimethyloctyl chloride (186.32 g; 212.94 ml; 1.05 mol) was added over the course of 3 minutes via a dropping funnel. The mixture was stirred at RT for a further 2 hours and subsequently stirred at an internal temperature of 80° C. for 96 hours. Ethanol was distilled off. The residue was taken up in ethyl acetate, and the precipitate was separated off by filtration. The organic phase was extracted three times with 10% strength by weight aqueous NaOH solution and washed once with H2O, three times with H2O which had been acidified using CO2 and again with H2O. After the mixture had been dried using MgSO4, the solvent was stripped off again in a rotary evaporator, and the crude product was purified by fractional distillation under reduced pressure.

Provenance & Evidence