Methanol → Methyl 3,4-dimethoxycinnamate

HRID 1272269

反応式

HRID 1272269 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(Cl)(Cl)=O.[CH3:20]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([O:15][CH3:20])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

4

反応物 3

HCID 887MethanolHCID 168483',4'-Dimethoxycinnamic acidHCID 24386Thionyl Chloride

生成物 1

HCID 94307Methyl 3,4-dimethoxycinnamate収率 80%

反応条件

温度
60 °C

実験手順

To a suspension of 3-(3,4-dimethoxyphenyl)-2-propenoic acid (21.8 g, 105 mmol) in methanol (220 ml) was added thionyl chloride (23.0 mL, 315 mmol) under ice cooling and the mixture was stirred at 60° C. for 12 hours. The resulting mixture was concentrated under reduced pressure, and the residue was added to water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain 18.7 g (yield 80%) of the title compound. mp. 72–74° C.

後処理

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionthe residue was added to water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-b82b9fe6b0b34087a1915e45f917ac45
出典データセット
uspto-grants-2007_04
特許番号
US07208495B2

関連ノート

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