Project Description:

• To reduce benzil to hydrobenzoin (phase one) and analyze/verify the product; then
synthesize stilbenediol acetonide from that hydrobenzoin (phase two) and
analyze/verify that product.

Synthesis Plan:

• Phase One: Benzil to Hydrobenzoin (1,2-diphenylethane-1,2-diol)

*We will reduce benzil (in ethanol) with sodium borohydride, to produce
hydrobenzoin (1,2-diphenylethane-1,2-diol). The solution will be filtered (if
necessary), then set aside to crystallize.

• Phase Two: Hydrobenzoin to Stilbenediol acetonide (2,2-dimethyl-1,5-dioxolane)

*We will take the hydrobenzoin produced in phase one, dissolve it in acetone
(acetone is solvent and reactant) and add iron (III) chloride as a catalyst. We will
heat the solution to form the stilbenediol acetonide. The solution will be poured
into water (that contains a base that will react with the acid) and the product will
be extracted with dichloromethane. The product will be crystallized in hexane and
cooled, collected, and dried.

Purification Determination (for phase one-- benzil to hydrobenzoin step):

• Melting Point Determination—the MP of hydrobenzoin should be 136-
137 degrees Celsius
• Thin-layer chromatography—our Rf value should be between .3 and .7; our pure
product should only make one spot (not multiple spots)

Verification (for phase one-- benzil to hydrobenzoin step):

• IR Spectroscopy—looking especially the for spectra show absorptions for O-H,
the benzene ring/aromatic carbons, and the C-O bond
*O-H bond: 3400-3650 cm-1
*Benzene Ring/Aromatic Carbons: 3030 cm-1 and 1660-2000 cm-1 (both weak)/
1450-1600 cm-1 (medium)
*C-O stretch: 1050-1150 cm-1 (strong)
• Mass Spectroscopy—the molecular weight of hydrobenzoin should be 214.25; if
different ion fragments are shown on the spectra, we can determine the structure
of the compound (and confirm that we have hydrobenzoin) by observing how it
fragments

Purification Determination (for phase two-- hydrobenzoin to stilbenediol acetonide step):

• Thin-layer chromatography—our Rf value should be between .3 and .7; our pure
product should only make one spot (not multiple spots) when viewed under UV
light
 • Gas chromatography—our product should show only one peak (with maybe a
small peak for air); we should have only one isomer of stilbenediol acetonide
present (making only one peak)

Verification (for phase two-- hydrobenzoin to stilbenediol acetonide step):

• IR Spectroscopy—looking especially the for spectra show absorptions for the
benzene ring/aromatic carbons, the C-O bond
*Benzene Ring/Aromatic Carbons: 3030 cm-1 and 1660-2000 cm-1 (both weak)/
1450-1600 cm-1 (medium)
*C-O stretch: 1050-1150 cm-1 (strong)
• Mass Spectroscopy—the molecular weight of stilbenediol acetonide should be
approximately 254.3; if different ion fragments are shown on the spectra, we can
determine the structure of the compound (and confirm that we have stilbenediol
acetonide) by observing how it fragments

Chemicals:
• Benzil
• 95% Ethanol
• Sodium Borohydride
• Solid Sodium Chloride
• Acetone
• Anhydrous Iron (III) Chloride
• 3M Potassium Carbonate
• Granular Anhydrous Calcium Chloride
• Dichloromethane
• Hexane

Special Materials:
• Wilfilter
• Small separatory funnel
• Viton connector
• Pipe cleaner
• Air condenser