Dimethyl Sulfoxide → Benzil

HRID 991270Notes

Reaction equation

HRID 991270 reaction equation
CS(C)=O.[C:5]1([C:11]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:14])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>C(OCC)(=O)C>[C:15]1([C:13]([C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:12])=[O:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8400Benzoin

Product 1

HCID 8651BenzilYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While the temperature is maintained at from 2° C. to 25° C., 16 g of the composition prepared as in Example 8 are added in small fractions over a period of 15 minutes to 35 ml of dimethyl sulfoxide containing 4.8 g of benzoin. After 2 hours, agitation at ambient temperature, the medium is poured into 200 ml of water and 60 ml of ethyl acetate. The precipitate formed is eliminated and the organic phase is concentrated under vacuum. The solid residue is recrystallised from 20 ml of ethanol. Benzil is obtained with a yield of 78%.

Workup

  1. temperatureWhile the temperature is maintained at from 2° C. to 25° C., 16 g of the composition prepared as in Example 8
  2. customThe precipitate formed
  3. concentrationthe organic phase is concentrated under vacuum
  4. customThe solid residue is recrystallised from 20 ml of ethanol

Sources & evidence

ORD record
ord-acd95e5e9b0a4044853045bc6fc6cd34
Source dataset
uspto-grants-2002_10
Patent number
US06462227B2

Reaction notes

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