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

HRID 534760Notes

Reaction equation

HRID 534760 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

N-[4-(Hydroxymethyl)-3-methylphenyl]acetamide (D77) (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 for 7 minutes. The MnO2 was filtered off and the reaction mixture was concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% ethyl acetate/petroleum ether yielded the title compound as a cream solid (0.326 g). δH (CDCl3, 400 MHz) 10.17 (1H, s), 7.77 (1H, d), 7.51 (1H, d), 7.45 (1H, s), 7.36 (1H, br.s), 2.66 (3H, s), 2.22 (3H, s). MS (ES): MH+ 178.2.

Workup

  1. filtrationThe MnO2 was filtered off
  2. concentrationthe reaction mixture was concentrated
  3. customto give the crude product which
  4. customwas purified by column chromatography
  5. washElution with 0-100% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-f6dd7cd0e5a146878c250bf331eefd96
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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