Nitromethane → HCID 59370485, compound

HRID 2383303Notes

Reaction equation

HRID 2383303 reaction equation
[CH3:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[NH4+].[N+:17]([CH3:20])([O-:19])=[O:18]>>[CH3:1][C:2]1[C:3](/[CH:4]=[CH:20]/[N+:17]([O-:19])=[O:18])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 131626633-Methoxy-2-methylbenzaldehyde

Product 1

HCID 59370485HCID 59370485, compound

Conditions

Temperature
100 °C

Procedure

To a solution of 2-methyl-3-(methyloxy)benzaldehyde (available from Allichem Product List; 20.0 g; 133 mmol) in nitromethane (400 ml) was added ammonium acetate (6.16 g; 80.0 mmol) and the resulting orange mixture was stirred for 1 h at 100° C. then cooled to room temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate (×2) and brine, and the organic layers washed with brine, dried (MgSO4) and concentrated in vacuo. Trituration with dichloromethane/ether gave the title compound as a yellow solid (6.60 g).

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (×2) and brine
  4. washthe organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad03a732fa6f421cab36ce905f7aa859
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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