Sulfuric Acid → Phenylbenzoin

HRID 28088

Reaction equation

HRID 28088 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS(O)(=O)=O.C(Cl)(Cl)Cl>C(OCC)C>[C:17]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:9]([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[OH:8])=[O:10])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6212ChloroformHCID 8651BenzilHCID 178418255HCID 178418255, compound

Product 1

HCID 19793701PhenylbenzoinYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

168.18 g (1.0 mole) of benzil in 2 liters of ethyl ether was placed in a 5 liter, three necked round bottomed flask, fitted with a reflux condenser, mechanical stirrer, addition funnel and nitrogen bypass. All of the glassware was flame-dried before use while being flushed with nitrogen. A 3 molar solution in ethyl ether of phenyl magnesium bromide (181.23 g, 1.0 mole) was then placed in the addition funnel and added dropwise to the flask over a period of 1.5 hours. The solution was then refluxed overnight. Hydrolysis of the Grignard complex was then accomplished using a 10% solution of H2SO4 with the concurrent addition of 1.5 liters of CHCl3. After complete hydrolysis, the organic layer was separated and washed with one liter of water. The organic layer was dried with magnesium sulfate, concentrated and recrystallized with hexane to give phenylbenzoin (m.p. 87°-88°, lit 88° C.) of 99% purity in yield of 62%.

Workup

  1. customfitted with a reflux condenser, mechanical stirrer, addition funnel
  2. customAll of the glassware was flame-dried before use
  3. customwhile being flushed with nitrogen
  4. additionadded dropwise to the flask over a period of 1.5 hours
  5. temperatureThe solution was then refluxed overnight
  6. customHydrolysis of the Grignard complex
  7. customAfter complete hydrolysis
  8. customthe organic layer was separated
  9. washwashed with one liter of water
  10. dry with materialThe organic layer was dried with magnesium sulfate
  11. concentrationconcentrated
  12. customrecrystallized with hexane

Sources & evidence

ORD record
ord-49a9f33ff08140878aa02982278d0961
Source dataset
uspto-grants-1980_09
Patent number
US04225528

Linked notes

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