Dimethyl Sulfoxide → Dibenzoylmethane

HRID 2225985Notes

Reaction equation

HRID 2225985 reaction equation
C[O-].[Na+].CS(C)=O.[C:8]([O:16]C)(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH3:19]>CO.O1CCOCC1>[C:21]1([C:18](=[O:20])[CH2:19][C:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:16])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7150Methyl BenzoateHCID 7410AcetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 8433Dibenzoylmethane

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

An apparatus as described in Example 1 is charged with 18.0 g of sodium methylate (97%), 100 g of DMSO, 100 g of dioxane and 6 g of methanol and the mixture is cooled to 0° C. Then a mixture of 45 g of methyl benzoate and 36 g of acetophenone are added dropwise over 35 minutes. The reaction mixture is then stirred for ca. 45-60 minutes at 30° C.

Workup

  1. additionare added dropwise over 35 minutes

Sources & evidence

ORD record
ord-5e59714a730c43e49f084563caf40d22
Source dataset
uspto-grants-1994_09
Patent number
US05344992

Reaction notes

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