Potassium Carbonate → [3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanone

HRID 2247888Notes

Reaction equation

HRID 2247888 reaction equation
[CH3:1][O:2][CH:3]([O:22][CH3:23])[C:4]1[CH:5]=[C:6]([CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)C#N)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-:25].[K+].[K+]>CN(C)C(=O)C>[CH3:1][O:2][CH:3]([O:22][CH3:23])[C:4]1[CH:5]=[C:6]([C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:25])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 198160313-(Dimethoxymethyl)-4-nitro-alpha-phenylbenzeneacetonitrile

Product 1

HCID 19816024[3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanoneYield 67.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 26.7 parts of intermediate 9, namely 3-(dimethoxymethyl)-4-nitro-α-phenylbenzeneacetonitrile, 12.3 parts of potassium carbonate and 360 parts of N,N-dimethylacetamide was stirred at room temperature while bubbling air through it. The reaction mixture was poured into water and the whole was extracted with dichloromethane. The extract was dried, filtered and evaporated and the residue was purified by column chromatography (silica gel; CHCl3 /hexane 80:20). The eluent of the desired fraction was evaporated, yielding 18.1 parts (67.3%) of [3-(dimethoxymethyl)-4-nitrophenyl]phenylmethanone (interm. 10).

Workup

  1. customwhile bubbling air through it
  2. additionThe reaction mixture was poured into water
  3. extractionthe whole was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by column chromatography (silica gel; CHCl3 /hexane 80:20)
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-fa2624b870434a03b915e85e110280e0
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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