Dimethylformamide → 2,2-Dimethoxy-2-phenylacetophenone

HRID 1577308Notes

Reaction equation

HRID 1577308 reaction equation
C[O-].[Na+].[C:4]1([C:10]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][O:21]S(C1C=CC(C)=CC=1)(=O)=O.[CH3:32]N(C)C=O>O>[CH3:32][O:13][C:12]([O:21][CH3:20])([C:10]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6645Methyl p-toluenesulfonateHCID 8651BenzilHCID 10942334Sodium Methoxide

Product 1

HCID 905712,2-Dimethoxy-2-phenylacetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6 parts of sodium methylate are added in portions in the course of 2 hours to a solution of 21 parts of benzil and 37 parts of p-toluenesulfonic acid methyl ester in 50 parts of dimethylformamide at room temperature, whilst stirring. The reaction mixture is then heated with 500 parts of water for 1 hour under reflux and subsequently cooled to room temperature, and the precipitate is filtered off and recrystallized from a mixture of isopropanol and water. 22 parts of benzil dimethylketal are obtained.

Workup

  1. temperatureunder reflux
  2. filtrationthe precipitate is filtered off
  3. customrecrystallized from a mixture of isopropanol and water

Sources & evidence

ORD record
ord-efd9e274eeac499bbcae1bbd7462a018
Source dataset
uspto-grants-1981_09
Patent number
US04287367

Reaction notes

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