Reduction of Benzoin

In a 25 mL Erlenmeyer flask benzoin (0.503 g) and ethanol (4.0 mL) was added and swirled until dissolved. Sodium borohydride (0.1 g) was added with a microspatula over five minutes. Mixture was gently swirled for 20 minutes. Mixture was cooled in ice-water bath. Water (5.0 mL) and 6 M HCl (0.3 mL) was added. Water (2.5 mL) was added 15 minutes later. Product was collected via vacuum filtration. Solid was washed with ice-cold water and dried on filter for 15 min. Crude yield and MP determined. Crude material (1.5 mg) was reserved for TLC. Crude solid was recrystallized from acetone with 25 mL Erlenmeyer flask. Melting point and percent yield was determined. Benzoin, recrystallized product, and crude product was dissolved in ethyl acetate in three vials. TLC plates was spotted and run in 9:1 CH2Cl2:ethanol in capped chamber until 1 cm from top. Spots viewed under UV light and marked.