Dimethyl Sulfoxide → Dibenzoylmethane

HRID 2225981Notes

Reaction equation

HRID 2225981 reaction equation
CS(C)=O.C[O-].[Na+].[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.COCCOCCOC>[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 8150DiglymeSolvent

Conditions

Temperature
30 °C

Procedure

100 g of anhydrous dimethyl sulfoxide, 100 g of diethylene glycol dimethyl ether, 6 g of absolute methanol and 18 g of sodium methylate (97%) are charged to an apparatus as described in Example 1. A mixture of 45 g of methyl benzoate and 36 g of acetophenone are added dropwise to this mixture at 25 ° C. over 45 minutes. After this addition, the reaction mixture is stirred for 2 hours at 30° C. and the solvent is removed by vacuum distillation at a temperature of <60 ° C. The residue is diluted with 150 g of methyl tert-butyl ether, cooled to 0° C. and filtered. The filter cake is washed twice with methyl tert-butyl ether. The pale grey solid is thereafter taken up in dilute hydrochloric acid and stirred.

Workup

  1. additionare added dropwise to this mixture at 25 ° C. over 45 minutes
  2. additionAfter this addition
  3. customthe solvent is removed by vacuum distillation at a temperature of <60 ° C
  4. additionThe residue is diluted with 150 g of methyl tert-butyl ether
  5. temperaturecooled to 0° C.
  6. filtrationfiltered
  7. washThe filter cake is washed twice with methyl tert-butyl ether
  8. stirringstirred

Sources & evidence

ORD record
ord-7aa95093c62b49afa58e240649ddd22e
Source dataset
uspto-grants-1994_09
Patent number
US05344992

Reaction notes

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