Sulfuric Acid → alpha,alpha-Bis-acetyloxy-4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]toluene

HRID 4742

반응식

HRID 4742 반응식
[F:1][C:2]([F:17])([F:16])[C:3]([C:9]1[CH:14]=[CH:13]C(C)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].S(=O)(=O)(O)O.[C:23]([O:26][C:27](=[O:29])[CH3:28])(=[O:25])[CH3:24]>O.[O-2].[O-2].[O-2].[Cr+6]>[C:23]([O:26][CH:27]([O:29][C:27](=[O:26])[CH3:28])[C:28]1[CH:11]=[CH:10][C:9]([C:3]([O:8][C:23](=[O:25])[CH3:24])([C:2]([F:1])([F:16])[F:17])[C:4]([F:5])([F:6])[F:7])=[CH:14][CH:13]=1)(=[O:25])[CH3:24]

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 7918Acetic Anhydride2회HCID 748292-(p-Tolyl)hexafluoroisopropanol

생성물 1

HCID 14076668alpha,alpha-Bis-acetyloxy-4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]toluene

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 962Water용매2회

실험 절차

To a solution of 156 g (0.60 mole) of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]toluene in 675 ml of acetic anhydride is added 135 ml of concentrated sulfuric acid at 0°. To the solution stirred at 0° is added a soluton of 168 g (1.68 mole) of chromium trioxide in 750 ml of acetic anhydride dropwise over a two-hour period. After stirring is continued for an additional two hours, the resulting reaction mixture is poured into five liters of ice and is diluted with five liters of water to obtain an aqueous mixture which is allowed to stand for 18 hours. An oily solid with water above it is obtained. Water is decanted from the oily solid. The solid is dissolved in ether to obtain a solution which is washed with water and sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to give an oily solid. The solid is triturated with ether, filtered and recrystallized from chlorobutane to give 60 g of α,α -bis-acetyloxy-4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]toluene, m.p. 93°-94.6°.

후처리

  1. stirringAfter stirring
  2. customthe resulting reaction mixture
  3. customto obtain an aqueous mixture which
  4. waitto stand for 18 hours
  5. customWater is decanted from the oily solid
  6. dissolutionThe solid is dissolved in ether
  7. customto obtain a solution which
  8. washis washed with water and sodium bicarbonate solution
  9. dry with materialdried with anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated at reduced pressure
  12. customto give an oily solid
  13. customThe solid is triturated with ether
  14. filtrationfiltered
  15. customrecrystallized from chlorobutane

출처 및 근거

ORD 기록
ord-444e854447fe4b53ac481a298adcab6e
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727180

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