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

HRID 228364Notes

Reaction equation

HRID 228364 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

Dissolve 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) in acetic acid (9 mL). Heat the reaction mixture at 110° C. for 2 hours. Concentrate the reaction mixture under reduced pressure and partition the residue between ether and water. Separate the layers and dry with Na2SO4, filter and concentrate under reduced pressure to afford a crude product. Purify the crude by flash chromatography (eluent: EtOAc/hexane 20/80 and 30/70) to afford 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. concentrationConcentrate the reaction mixture under reduced pressure
  2. custompartition the residue between ether and water
  3. customSeparate the layers
  4. dry with materialdry with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto afford a crude product
  8. customPurify the crude by flash chromatography (eluent: EtOAc/hexane 20/80 and 30/70)

Sources & evidence

ORD record
ord-b5ec2c820e894fb8b381cce4e5005108
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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