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

HRID 130945ノート

反応式

HRID 130945 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 534242052-Methyl-4-(2-nitrovinyl)phenol収率 88.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-04183baffec14fae86bc97166ce25056
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

反応ノート

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