3-Methyl-4-nitrobenzyl alcohol → 3-Methyl-4-nitrobenzaldehyde

HRID 2203292Notes

Reaction equation

HRID 2203292 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 5913603-Methyl-4-nitrobenzyl alcohol

Product 1

HCID 111945283-Methyl-4-nitrobenzaldehydeYield 87.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A flask was charged with (3-methyl-4-nitro-phenyl)-methanol (66.9 g, 0.400 mol), manganese(IV) oxide (85%, 5 μm powder, 409.1 g, 4.00 mol), and CH2Cl2 (1337 mL). The mixture was stirred at 40° C. for at least 2 h or until HPLC analysis showed that the reaction had proceeded to greater the 97% completion. The cooled batch was diluted with CH2Cl2 (1 L) and filtered through a Celite® pad (34 g), and the filter cake was rinsed with more CH2Cl2 (1 L). The filtrate and washes were concentrated under in vacuo to dryness to give the title compound as a yellow solid (58 g, 87% yield).

Workup

  1. filtrationfiltered through a Celite® pad (34 g)
  2. washthe filter cake was rinsed with more CH2Cl2 (1 L)
  3. concentrationThe filtrate and washes were concentrated under in vacuo to dryness

Sources & evidence

ORD record
ord-2fe7b97dacba4d4fad42aad212d0ab47
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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