(2-Methyl-4-nitrophenyl)methanol → 2-Methyl-4-nitrobenzaldehyde

HRID 2203297Notes

Reaction equation

HRID 2203297 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][OH:12]>[O-2].[Mn+4].[O-2].C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 21345674(2-Methyl-4-nitrophenyl)methanol

Product 1

HCID 126541462-Methyl-4-nitrobenzaldehydeYield 78.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A flask was charged with (2-methyl-4-nitro-phenyl)-methanol (16.7 g, 0.100 mol) (334 mL), to manganese(IV) oxide (5 μm, 102.3 g, 1.00 mol), and CH2Cl2 (334 mL). The stirred mixture was heated at 40° C. for at least 2 h or until in-process HPLC analysis showed that conversion was greater than 95%. The cooled mixture was filtered through a celite cake (8 g) loaded onto a fritted funnel and the filter cake was rinsed with CH2Cl2 (340 mL). The filtrate and wash were concentrated under reduced pressure to dryness to afford the title compound as an amorphous solid (13.0 g, 78% yield).

Workup

  1. filtrationThe cooled mixture was filtered through a celite cake (8 g)
  2. customloaded onto a fritted funnel
  3. washthe filter cake was rinsed with CH2Cl2 (340 mL)
  4. washThe filtrate and wash
  5. concentrationwere concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-b900765e8dcd470fbd8412bf6cdb982a
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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