Benzyl Alcohol → 2-Benzyl-D-arabinose

Participants

Reaction Conditions

Reaction Steps

D-Arabinose (50 kg, 330.04 moles) and benzyl alcohol (132.2 kg, 4.33 equivalents) were stirred and heated to 35° C. Acetyl chloride (10.9 kg, 0.42 equivalents) was added slowly, keeping the temperature <45° C., then stirred 50° C. overnight. The mixture was cooled to 20° C. and diluted with MTBE (600 kg). The mixture was stirred for 0.5-5 h. The solids were collected by filtration and washed with MTBE (2×40 kg). The material was dried in a filter drier. 2-Benzyl-D-arabinose (1) was obtained as an off-white solid, 70.9 kg (88.6%). 1H NMR (300 MHz, DMSO-d6): δ 7.32 (m, 5H), 4.76 (s, 1H), 4.66 (d, J=12 Hz, 1H), 4.59 (m, 3H), 4.45 (d, J=12 Hz, 1H), 3.70 (m, 4H), 3.47 (dd, J=12, 3 Hz, 1H).

Provenance & Evidence