Nitromethane → 2-Methyl-4-(2-nitrovinyl)phenol

HRID 130945

Reaction equation

HRID 130945 reaction equation
C[C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:11]([CH3:14])([O-:13])=[O:12].[C:15]([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:15][C:9]1[CH:2]=[C:3]([CH:4]=[CH:14][N+:11]([O-:13])=[O:12])[CH:6]=[CH:7][C:8]=1[OH:10]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 4581854-Hydroxy-2-methylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 534242052-Methyl-4-(2-nitrovinyl)phenolYield 88.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

The 2-methyl-4-hydroxy-benzaldehyde (980 mg, 6.3 mmol), nitromethane (2.0 mL, 37.7 mmol) and ammonium acetate (1.9 g, 25.1 mmol) were dissolved in acetic acid (9 mL) and the reaction heated at 110° C. for 2 h. The reaction is concentrated under reduced pressure and the residue partitioned between ether and water. Separate the layers and dry with Na2SO4, filter and concentrate under reduced pressure. Purify the crude by flash chromatography (eluent: EtOAc/hexane 20/80 and 30/70) afforded the title compound (1.0 g). 1H-NMR (CDCl3, 200 MHz): 7.94 (d, 1H, J=13.4 Hz), 7.50 (d, 1H, J=13.6 Hz), 7.34-7.27 (m, 2H), 6.82 (d, 1H, J=8.1 Hz), 2.28 (s, 3H).

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. customthe residue partitioned between ether and water
  3. customSeparate the layers
  4. dry with materialdry with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify the crude by flash chromatography (eluent: EtOAc/hexane 20/80 and 30/70)

Sources & evidence

ORD record
ord-04183baffec14fae86bc97166ce25056
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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