Trifluoroacetic acid → 10,11-dihydro-10,10,11,11-tetrafluoro-5H-dibenzo[a,d]cyclohepten-5-one

HRID 329231노트

반응식

HRID 329231 반응식
[F:1][C:2]1([F:19])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]1([F:18])[F:17].FC(F)(F)C(O)=[O:23]>[O-2].[O-2].[O-2].[Cr+6].C(O)(=O)C>[F:1][C:2]1([F:19])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[O:23])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]1([F:17])[F:18]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 2037334410,11-dihydro-10,10,11,11-tetrafluoro-5H-dibenzo[a,d]cycloheptene

생성물 1

HCID 2037337610,11-dihydro-10,10,11,11-tetrafluoro-5H-dibenzo[a,d]cyclohepten-5-one

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매2회HCID 176Acetic Acid용매

실험 절차

A mixture of 1.45 g. (0.00544 mole) of 10,11-dihydro-10,10,11,11-tetrafluoro-5H-dibenzo[a,d]cycloheptene, 0.73 g. (0.0073 mole) of chromium trioxide, 25 ml. of trifluoroacetic acid and 2 ml. of glacial acetic acid is stirred at reflux for 21/4 hours. During this period, almost all of the chromium trioxide dissolves. Solvents are evaporated under reduced pressure and the residue is partitioned between benzene and water. The aqueous layer is separated and re-extracted twice with benzene. The combined benzene extracts are washed thoroughly with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The crude product is left as the residual oily solid and is purified by column chromatography on 75 g. of silica gel, eluting the product with 1:1 benzene-carbon tetrachloride. The fractions that show one spot of Rf 0.75 on a silica thin layer plate developed with benzene are combined. Evaporation of the solvent under reduced pressure leaves the white crystalline product, m.p. 70°-75° C.

후처리

  1. additionA mixture of 1.45 g
  2. temperatureat reflux for 21/4 hours
  3. waitDuring this period
  4. customSolvents are evaporated under reduced pressure
  5. customthe residue is partitioned between benzene and water
  6. customThe aqueous layer is separated
  7. extractionre-extracted twice with benzene
  8. washThe combined benzene extracts are washed thoroughly with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated to dryness under reduced pressure
  11. waitThe crude product is left as the residual oily solid
  12. customis purified by column chromatography on 75 g
  13. washof silica gel, eluting the product with 1:1 benzene-carbon tetrachloride
  14. customEvaporation of the solvent under reduced pressure
  15. customleaves the white crystalline product, m.p. 70°-75° C.

출처 및 근거

ORD 기록
ord-6fe0d95a82ee48cf9528e95ea746a63c
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04020096

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