Dimethyl Sulfoxide → 4-Methoxybenzaldehyde

HRID 271987Notes

Reaction equation

HRID 271987 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.CS(C)=[O:12].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+]>C(#N)C.O.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[O:12])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 679Dimethyl SulfoxideHCID 77314-MethylanisoleHCID 62655Sodium Persulfate

Product 1

HCID 312444-Methoxybenzaldehyde

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

In a 100 ml reactor containing argon gas, 2.44 g of 1-methoxy-4-methylbenzene (CAS Registration No. 104-93-8) [20 mmol] is dissolved in 39 ml of acetonitrile, with the addition of 1.0 ml of dimethyl sulfoxide [14.1 mmol] at 70° C. To the solution, 65 mg of Cu(OAc)2, 30 mg of FeSO4.7 H2O and 10 ml of water are added. Next, while stirring forcefully, 11.0 g of Na2S2O8, dissolved in 30 ml of water, are then added drop by drop. The reaction is ended after 120 minutes.

Workup

  1. additionare then added drop by drop

Sources & evidence

ORD record
ord-d189a08a923f4bacb1cd80dfc2529588
Source dataset
uspto-grants-2008_11
Patent number
US07453013B2

Reaction notes

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