N-[4-(hydroxymethyl)-3-methylphenyl]acetamide → N-(4-Formyl-3-methylphenyl)acetamide

HRID 2424627Notes

Reaction equation

HRID 2424627 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13]>C(#N)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13])=[O:1]

Participants

4

Reactant 1

HCID 54053024N-[4-(hydroxymethyl)-3-methylphenyl]acetamide

Product 1

HCID 12931765N-(4-Formyl-3-methylphenyl)acetamideYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

D4 (0.36 g, 2 mmol) and manganese dioxide (0.875 g, 10 mmol) were combined in acetonitrile (16 mL) and heated to 120° C. in the microwave. The solid residue was filtered off and the reaction mixture concentrated. The crude product was purified by column chromatography. Elution with 0-100% EtOAc/petroleum ether yielded the title compound as a cream solid (0.326 g). δH (CDCl3, 400 MHz) 10.27 (1H, s), 7.79 (1H, d), 7.50 (1H, d), 7.45 (1H, s), 7.35 (1H, br.s), 2.66 (3H, s), 2.20 (3H, s). MS (ES+): MH+ 178.2.

Workup

  1. filtrationThe solid residue was filtered off
  2. concentrationthe reaction mixture concentrated
  3. customThe crude product was purified by column chromatography
  4. washElution with 0-100% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-1cbeaf8028d64431994488baae58f1bb
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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