Cornforth reagent → 4-Methyl-2-nitrobenzaldehyde

HRID 1969005Notes

Reaction equation

HRID 1969005 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 53405041(4-Methyl-2-nitrophenyl)methanol

Product 1

HCID 5904464-Methyl-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Methyl-2-nitrophenyl)methanol D139 (1.028 g, 6.15 mmol), pyridinium dichromate (3.47 g, 9.22 mmol)+molecular sieves (7 g, 6.15 mmol) in dry dichloromethane (DCM) (14 mL) was stirred under argon at R.T. overnight. The reaction mixture was filtered by silica/kieselguhr (1:1) and extracted with water and DCM. Organic layers were combined and evaporated to give a pale yellow solid which was used without further purification (0.665 g, 65.5%).

Workup

  1. filtrationThe reaction mixture was filtered by silica/kieselguhr (1:1)
  2. extractionextracted with water and DCM
  3. customevaporated
  4. customto give a pale yellow solid which
  5. customwas used without further purification (0.665 g, 65.5%)

Sources & evidence

ORD record
ord-ed71939f77764575a60ec84485d0a896
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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