Chemical Properties
white crystalline powder
Uses
2,3-Dichlorobenzyl alcohol may be used in the preparation of methyl [2,3-dichlorobenzyl 4,7,8-tri-
O-acetyl-9-azido-3,5,9-trideoxy-5-(2-nitrophenylsulfonamido)-D-glycero-α-D-galacto-2-nonulopyranosid]onate and methyl [2,3-dichlorobenzyl 5-acetamido-4,7,8-tri-
O-acetyl-3,5,9-trideoxy-9-(4-phenylbenzamido)-D-glycero-α-D-galacto-2-nonulopyranosid]onate.
General Description
2,3-Dichlorobenzyl alcohol is also referred to as (2,3-dichlorophenyl)methanol (IUPAC name). It is mildly antiseptic in nature.
Synthesis
1. To a solution of 2,3-dichlorobenzaldehyde (500 g, 2.85 mol) in methanol (3.5 L) was slowly added an alkaline solution of sodium borohydride (113.5 g, 2.975 mol) dissolved in 0.2 N sodium hydroxide solution (241 mL) at 0°C. The addition process lasted for 1 hour. The reaction mixture was stirred at room temperature for 2 hours. Subsequently, the reaction mixture was quenched by slowly pouring it into water (3.7 L) and the pH was adjusted to 6 with glacial acetic acid (125 mL). the precipitated white solid was collected by filtration to afford 2,3-dichlorobenzyl alcohol (467 g, 92% yield).
References
[1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 564 - 576
[2] Patent: US6124308, 2000, A
[3] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
