what is the chemical reaction for this procedure?

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what is the chemical reaction for this procedure?

Procedure: Synthesis of hydrobenzoin from benzil
Dissolve benzil (1.5 g) in absolute ethanol (15 mL) in a 125-mL Erlenmeyer flask by swirling occasionally. Add sodium borohydride (300 mg) in small
portions over 3-5 min and continue swirling the contents over 20 min. Add water (30 mL) and cool the reaction mixture to 0 °C. Add conc. aq HCI
dropwise (slowly) until gas evolution ceases then continue stirring for 15 min. Filter the crude product by vacuum filtration and wash with cold water.
Collect melting point of the dried product.
Procedure: Synthesis of acetonide of hydrobenzoin
Important: Re-scale the procedure to use 4.0 mmol of hydrobenzoin.
In an oven-dried, 100-mL round-bottom flask containing magnetic stirring bar was added hydrobenzoin (1.0 g, 4.7 mmol), anhydrous iron(III) chloride (0.3
g, 1.8 mmol), and anhydrous acetone (30 mL). The mixture was heated and reflux was maintained for 30 min (with stirring). The reaction mixture was
cooled to rt and filtered through a pad of Celite(TM). The mother liquor was poured into a separatory funnel containing 10% aq potassium carbonate (20
mL). Water (80 mL) was added and the aqueous solution was extracted with dichloromethane (2 x 20 mL). The combined organic extracts were washed
with water (25 mL), brine (20 mL), dried with anhydrous sodium sulfate. The extract can be kept over anhydrous sodium sulfate for up to 3-5 days.
The solution containing acetonide was concentrated and to the residue was added petroleoum ether (15-20 mL) and the solids were filtered through a
glass wool plug (hot flitration). The collected solution was concentrated to approximately 5 mL and then cooled to 0 °C to initiate crystallization. The
product was collected by vacuum filtration to give the acetonide as a white crystalline solid.
Transcribed Image Text:Procedure: Synthesis of hydrobenzoin from benzil Dissolve benzil (1.5 g) in absolute ethanol (15 mL) in a 125-mL Erlenmeyer flask by swirling occasionally. Add sodium borohydride (300 mg) in small portions over 3-5 min and continue swirling the contents over 20 min. Add water (30 mL) and cool the reaction mixture to 0 °C. Add conc. aq HCI dropwise (slowly) until gas evolution ceases then continue stirring for 15 min. Filter the crude product by vacuum filtration and wash with cold water. Collect melting point of the dried product. Procedure: Synthesis of acetonide of hydrobenzoin Important: Re-scale the procedure to use 4.0 mmol of hydrobenzoin. In an oven-dried, 100-mL round-bottom flask containing magnetic stirring bar was added hydrobenzoin (1.0 g, 4.7 mmol), anhydrous iron(III) chloride (0.3 g, 1.8 mmol), and anhydrous acetone (30 mL). The mixture was heated and reflux was maintained for 30 min (with stirring). The reaction mixture was cooled to rt and filtered through a pad of Celite(TM). The mother liquor was poured into a separatory funnel containing 10% aq potassium carbonate (20 mL). Water (80 mL) was added and the aqueous solution was extracted with dichloromethane (2 x 20 mL). The combined organic extracts were washed with water (25 mL), brine (20 mL), dried with anhydrous sodium sulfate. The extract can be kept over anhydrous sodium sulfate for up to 3-5 days. The solution containing acetonide was concentrated and to the residue was added petroleoum ether (15-20 mL) and the solids were filtered through a glass wool plug (hot flitration). The collected solution was concentrated to approximately 5 mL and then cooled to 0 °C to initiate crystallization. The product was collected by vacuum filtration to give the acetonide as a white crystalline solid.
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