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

HRID 130945

반응식

HRID 130945 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-04183baffec14fae86bc97166ce25056
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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