Toluene → Benzene, (3-bromopropoxy)-

Participants

Reaction Steps

Bromophenol (996 g, 5.76 mmol), bromopropane (790 ml, 8.70 mmol) and tetrabutylammonium hydrogensulfate (19.6 g, 48.9 mmol) were dissolved slowly in 5 L of dimethyl sulfoxide. A solution resulting from dissolving sodium hydroxide (2300 g, 57.6 mmol) in 2300 g of water was dropped slowly. Since heat was generated during the above operation, the solution was added so that the internal temperature was kept at 40-45° C. After stirring at room temperature for 1 hour, the mixture was cooled to 25° C. and then 6.7 L of water was added while keeping at 20-30° C. After addition of 12 L of toluene, 3 L of tetrahydrofuran and 3.3 L of water, phase separation was conducted. The organic layer was washed with 8 L of water, two 4.2 L portions of a 20% brine and 8 L of water. After vacuum concentration, the residue was distilled under reduced pressure to yield p-bromopropoxybenzene (b.p. 96-100° C./4 mmHg, 1182.5 g, Yield 95.5%) as a colorless oily matter.

Provenance & Evidence