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

HRID 913211노트

반응식

HRID 913211 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-607190d3a7f8493cb166b904c9a6fb2f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026280B2

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