Dimethyl Sulfoxide → 4,4'-Dimethoxybenzil

HRID 1405334Notes

Reaction equation

HRID 1405334 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:19])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.CS(C)=[O:22]>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10](=[O:22])[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[O:19])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 67120Desoxyanisoin

Product 1

HCID 710434,4'-DimethoxybenzilYield 76%

Procedure

To a solution of 1,2-bis(4-methoxyphenyl)ethan-1-one (1 g, 3.90 mmol) in DMSO (20 mL) was added SeO2 (1.76 g, 15.86 mmol) in several batches at 100° C. over 30 min, and then stirred for 3 hr at this temperature. The reaction was quenched by the addition of water (200 mL) and extracted with dichloromethane (3×50 mL), dried over magnesium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (1%˜10% ethyl acetate in petroleum ether) to afford 1,2-bis(4-methoxyphenyl)ethane-1,2-dione as a brown solid (600 mg, 76%).

Workup

  1. customThe reaction was quenched by the addition of water (200 mL)
  2. extractionextracted with dichloromethane (3×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography (1%˜10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0ba4a0d7529748ce8d2af101709103ed
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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