3-Phenylprop-2-En-1-Ol → 2-Propenoic acid, 3-phenyl-, methyl ester

HRID 18903

反応式

HRID 18903 の反応式
[CH2:1]([OH:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(C1C(=O)C(Cl)=C(Cl)[C:15](=[O:16])C=1C#N)#N>CO>[C:1]([O:16][CH3:15])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 3083-Phenylprop-2-En-1-OlHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone

生成物 1

HCID 76442-Propenoic acid, 3-phenyl-, methyl ester収率 86%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A homogeneous mixture containing cinnamyl alcohol (7.5 mmol), DDQ (22.5 mmol), MeOH (20 mL) is taken in a round bottom flask and catalytic amount of AMBERLYST® 15 (0.1 g) is added to it. The mixture is stirred for 20 hrs at room temperature. After completion of the reaction (observed by TLC and by GC analysis), the reaction mixture is filtered and washed with MeOH (5 ml×2). Concentrate the filtrate under reduced pressure and the crude product thus obtained is loaded on a neutral alumina column and eluted with diethyl ether. Methyl cinnamate is isolated in 86% yield whose NMR values are found matching with reported values as in example 1.

後処理

  1. customis taken in a round bottom flask
  2. customAfter completion of the reaction (observed by TLC and by GC analysis)
  3. filtrationthe reaction mixture is filtered
  4. washwashed with MeOH (5 ml×2)
  5. concentrationConcentrate the filtrate under reduced pressure
  6. customthe crude product thus obtained
  7. washeluted with diethyl ether

出典と根拠

ORDレコード
ord-b4f61b10556843b39eda82f6c010d46e
出典データセット
uspto-grants-2010_06
特許番号
US07741508B2

関連ノート

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