Benzil → Hydrobenzoin

HRID 1796957Notes

Reaction equation

HRID 1796957 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.[BH4-].[Na+]>CCO.O>[C:11]1([CH:9]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:8])[OH:10])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 8651BenzilHCID 4311764Sodium borohydride

Product 1

HCID 95447Hydrobenzoin

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

To a slurry of 97.0 g of benzil in 1 liter of 95% EtOH was added 20 g of sodium borohydride. After stirring 10 minutes, the mixture was diluted with 1 liter of water and the mixture was treated with activated carbon. The mixture was then filtered trough supercel and the filtrate heated and diluted with an additional 2 liters of water until it became slightly cloudy. The mixture was then cooled to 0 to 5° C. and the resulting crytals were collected and washed with cold water. The crystals were then dried in vacuo.

Workup

  1. additionthe mixture was treated with activated carbon
  2. filtrationThe mixture was then filtered trough supercel
  3. temperaturethe filtrate heated
  4. additiondiluted with an additional 2 liters of water until it
  5. customthe resulting crytals were collected
  6. washwashed with cold water
  7. customThe crystals were then dried in vacuo

Sources & evidence

ORD record
ord-7f1fdae056914c53929bc0162e0ff096
Source dataset
uspto-grants-2006_04
Patent number
US07034026B2

Reaction notes

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