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

HRID 341857

反応式

HRID 341857 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 811345-Nitrovanillin

生成物 1

HCID 120806463-Methoxy-4-propoxy-5-nitrobenzaldehyde収率 57%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7b2a21f1c1314b4aaf26a3090406351c
出典データセット
uspto-grants-1999_01
特許番号
US05856323

関連ノート

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