Phosphorus oxychloride → 3-Methyl-5-phenyl-2,4-pentadienoic acid

HRID 1176100

反応式

HRID 1176100 の反応式
P(Cl)(Cl)(Cl)=O.[C:6]1([CH:12]=[CH:13][C:14]([CH3:17])(O)[CH3:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:18]([O-:21])(=[O:20])C.[Na+]>CN(C)C=O.O>[CH3:15][C:14]([CH:13]=[CH:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH:17][C:18]([OH:21])=[O:20]

参加物

6

反応物 3

HCID 24813Phosphorus oxychlorideHCID 926773-Methyl-1-phenyl-buten-3-olHCID 517045Sodium Acetate

生成物 1

HCID 7749383-Methyl-5-phenyl-2,4-pentadienoic acid収率 63.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Dimethylformamide (DMF, anhydrous, 25 mL) was cooled to 0-5° C. and phosphorus oxychloride (16.4 mL) was added dropwise over a period of an hour. The resulting solution was added dropwise to a cooled (0-5° C.) solution of 4-phenyl-2-methyl-3-buten-2-ol (0.14 mol) in 60 mL of anhydrous DMF over a period of an hour. The reaction mixture was then warmed to room temperature, gradually heated up to 80° C., stirred at 80° C. for three hours and cooled to 0-5° C. To the cooled reaction solution was added dropwise a solution of sodium acetate (80 g) in deionized water (190 mL) over a period of two hours. The mixture was then reheated to 80° C., stirred at 80° C. for an additional 10 minutes, cooled down to room temperature and extracted with ether (300 mL) twice. The combined extract was washed with water (200 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to yield 16.7 g of the desired 3-methyl-5-phenyl-2,4-pentadienal as a liquid which was used in the next step without further purification.

後処理

  1. additionThe resulting solution was added dropwise to
  2. temperaturegradually heated up to 80° C.
  3. temperaturecooled to 0-5° C
  4. customTo the cooled reaction solution
  5. customwas then reheated to 80° C.
  6. stirringstirred at 80° C. for an additional 10 minutes
  7. temperaturecooled down to room temperature
  8. extractionextracted with ether (300 mL) twice
  9. extractionThe combined extract
  10. washwas washed with water (200 mL)
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-910c52e50f3544bb99532884d2a6fe7e
出典データセット
uspto-grants-2010_11
特許番号
US07842727B2

関連ノート

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