Potassium Carbonate → 3-Methoxy-4-propoxy-5-nitrobenzaldehyde

HRID 341857

반응식

HRID 341857 반응식
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH2:22][CH3:23]>CN(C)C=O>[CH3:13][O:12][C:6]1[CH:7]=[C:8]([CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[O:14][CH2:21][CH2:22][CH3:23])[CH:9]=[O:10]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 811345-Nitrovanillin

생성물 1

HCID 120806463-Methoxy-4-propoxy-5-nitrobenzaldehyde수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 5-nitrovanillin (19.72 g, 100 mmol), potassium carbonate (35 g, 253.23 mmol) and propyl iodide (32.86 mL, 335.83 mmol) in 160 mL of N,N-dimethylformamide was stirred at 60° C. for 12 hours. The mixture was then cooled, quenched with water and extracted with methylene chloride. The organic layer was washed several times with water, dried over magnesium sulfate, filtered and evaporated in vacuo to an oil which was purified by flash chromatography on silica gel (230-400 mesh) using 2:1 hexane/ethyl acetate as eluent, to provide 3-methoxy-4-propoxy-5-nitrobenzaldehyde (13.54 g, 57%). 1H NMR (CDCl3): 1.00 (t, 3H), 1.85 (m, 2H), 4.00 (s, 3H), 4.25 (t, 2H), 7.65 (s, 1H), 7.85 (s, 1H), 9.95 (s, 1H).

후처리

  1. temperatureThe mixture was then cooled
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil which
  8. customwas purified by flash chromatography on silica gel (230-400 mesh)

출처 및 근거

ORD 기록
ord-7b2a21f1c1314b4aaf26a3090406351c
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856323

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