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

HRID 130911

反応式

HRID 130911 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

実験手順

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 eh 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).

後処理

  1. temperatureHeat
  2. customeh reaction mixture at 110° C. for 2 hours
  3. concentrationConcentrate the reaction mixture under reduced pressure
  4. custompartition the residue between ether and water
  5. customSeparate the layers
  6. dry with materialdry with Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customto afford a crude product
  10. 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-c53f7d05406f46d682e3dc4d9462bb37
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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