3,4-Dimethoxy-5-nitrobenzhydrol → 3,4-Dimethoxy-5-nitrobenzophenone

HRID 274441Notes

Reaction equation

HRID 274441 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[O:17][CH3:18])[CH:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[O:17][CH3:18])[C:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:13]

Participants

4

Reactant 2

HCID 214589923,4-Dimethoxy-5-nitrobenzhydrolHCID 178418287HCID 178418287, compound

Product 1

HCID 214590553,4-Dimethoxy-5-nitrobenzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g of 3,4-dimethoxy-5-nitrobenzhydrol dissolved in 50 ml of methylene chloride are treated with 2.2 g of pyridinium chlorochromate, whereupon the mixture is stirred at room temperature for 2 hours. The insoluble constituents are subsequently filtered. The filtrate is evaporated and the residue is chromatographed on 60 g of silica gel with methylene chloride. After crystallization from methylene chloride/hexane there is obtained 3,4-dimethoxy-5-nitrobenzophenone of m.p. 78°-80°.

Workup

  1. filtrationThe insoluble constituents are subsequently filtered
  2. customThe filtrate is evaporated
  3. customthe residue is chromatographed on 60 g of silica gel with methylene chloride
  4. customAfter crystallization from methylene chloride/hexane there

Sources & evidence

ORD record
ord-df04f892a15b4ff9a9ea3a10b0f09001
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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