Benzyl Alcohol → Benzyl mesylate

Participants

Reaction Conditions

Reaction Steps

Under nitrogen methylene chloride (1.4 liter), benzyl alcohol (129.6 g, 1.2 moles) and triethylamine (182 g, 1.8 moles) were combined, stirred and cooled to -5° C. in an ice-water-acetone bath. A solution of methanesulfonyl chloride (150 g, 1.31 moles) in 100 ml of methylene chloride was added over 49 minutes, maintaining the temperature between -5° and 2° C. After stirring for 10 minutes at 0°-2° C., the reaction was diluted with 500 ml of water, precooled to 5° C. The organic layer was separated, washed 2×500 ml of cold water, dried over MgSO4, filtered and evaporated in vacuo to yield title product as a light yellow oil [190 g; 85%; 1H-NMR (CDCl3) delta (ppm): 2.9 (s, 3H), 5.2 (s, 2H), 7.4 (m, 5H); Rf 0.75 (CH2Cl2 )]. This product was refrigerated until used in the next step.

Provenance & Evidence