Benzyl Chloride → 1,4-Bis(benzyloxy)-2-butene

Participants

Reaction Conditions

Reaction Steps

To 48% aqueous sodium hydroxide 127.8 g was added tetra-n-butylammonium bromide 3.3 g (10 mmol), and the mixture was heated to 60° C. To the mixture was added 2-butene-1,4-diol (14) 30.0 g (340 mmol), to which was added dropwise benzyl chloride 94.8 g (743 mmol) at 80±15° C. The mixture was stirred at the same temperature for 2 hours. The reaction mixture was cooled down, and separated after addition of water 90 ml. To the organic layer was add sulfuric acidic brine. The solution was neutralized by aqueous sodium hydrogen carbonate, separated, mixed with ethyl acetate, and concentrated under reduced pressure to yield the oil residue 104.5 g (quantitative) of the objective (15).

Provenance & Evidence