p-Toluenesulfonic acid → 3-Phenyl-2,4-pentanedione

HRID 1980314노트

반응식

HRID 1980314 반응식
B(F)(F)F.[C:5]([OH:8])(=O)[CH3:6].[C:9]1([CH2:15][C:16](=[O:18])[CH3:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OC(=O)C)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:9]1([CH:15]([C:5](=[O:8])[CH3:6])[C:16](=[O:18])[CH3:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 7678PhenylacetoneHCID 7918Acetic AnhydrideHCID 61423Hydrogen (acetato-O)trifluoroborate(1-)

생성물 1

HCID 2334023-Phenyl-2,4-pentanedione

실험 절차

Boron trifluoride-acetic acid (36%, 34.8 grams) was added with stirring dropwise to a solution of phenylacetone (4.46 grams), acetic anhydride, and para-toluenesulfonic acid (0.6 grams) in a water bath at room temperature. After stirring over night, a solid precipitate formed which was collected and washed with water and then refluxed in 100 ml water and sodium acetate (9.0 grams) for 2-3 hours. The original reaction mixture was also heated with 200 ml water and sodium acetate (13.5 grams) for the same period. Both mixtures were separately extracted with ether and then washed with saturated sodium bicarbonate solution to remove any acid. The ether portions were dried and then evaporated in vacuo leaving an oil which solidified, yield 1.4 grams, m.p. 40°-52° C.

후처리

  1. customa solid precipitate formed which
  2. customwas collected
  3. washwashed with water
  4. temperaturerefluxed in 100 ml water
  5. temperatureThe original reaction mixture was also heated with 200 ml water and sodium acetate (13.5 grams) for the same period
  6. extractionBoth mixtures were separately extracted with ether
  7. washwashed with saturated sodium bicarbonate solution
  8. customto remove any acid
  9. dry with materialThe ether portions were dried
  10. customevaporated in vacuo
  11. customleaving an oil which

출처 및 근거

ORD 기록
ord-d8ebe9cf80f445de813199f000d1950a
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04508722

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