benzoin - Name: Jordan Gales Teaching Assistant: Mathieu...

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Name : Jordan Gales Teaching Assistant: Mathieu Chellat Lab: T/R 8:30 a.m. – 420 CE Submitted: April 8 th , 2010 Purpose: To synthesize benzoin via a thiamine hydrochloride catalyzed benzoin condensation reaction of benzaldehyde. Reaction Scheme : Procedure : 1 A solution of thiamine-HCl (1.5 g, 4.45 mmol), water (2.00 mL), 95% ethanol (and 15.00 mL) sodium hydroxide (0.36 g, 9.00 mmol, and 4.5 mL) and benzaldehyde (4.70 g, 44.31 mmol) was reacted at room temperature (30°C) for 48 h. The crude mass was isolated via suction filtration and washed with cold water (20.0 mL). The crude benzoin was then recrystallized from hot ethanol using macroscale recrystallization technique to obtain benzoin (3.01 g, 14.17 mmol, 65%) as a white crystalline solid mp 135-136°C (lit mp 2 134-138°C). Discussion: Water, 95% ethanol, sodium hydroxide, and benzaldehyde were reacted with catalytic thiamine- HCl to yield benzoin as a white crystalline solid in 65% yield. The melting point range of the product was determined to be 135-136°C, which is within the reported literature range and
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benzoin - Name: Jordan Gales Teaching Assistant: Mathieu...

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