Tetrahydrofuran → 3,5-Dibenzyloxybenzyl methanesulfonate

Participants

Reaction Steps

Methanesulfonyl chloride (5.03 ml) was slowly added to a mixture of 3,5-dibenzyloxybenzyl alcohol (16.0 g), triethylamine (9.06 ml), and tetrahydrofuran (200 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The colorless crystals obtained were collected by filtration to yield 3,5-dibenzyloxybenzyl methanesulfonate (22.20 g, yield: 91%). This was recrystallized from ethyl acetate-hexane. Melting point: 85–86° C.

Provenance & Evidence