Methane → 9H-Fluoren-9-one, 2-fluoro-

HRID 1903873

반응식

HRID 1903873 반응식
[F:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[OH-:15].C([N+](C)(C)C)C1C=CC=CC=1.O=O.C>N1C=CC=CC=1>[F:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 297MethaneHCID 977OxygenHCID 66854Benzyltrimethylammonium hydroxideHCID 2411322-Fluorofluorene

생성물 1

HCID 960169H-Fluoren-9-one, 2-fluoro-

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

2-Fluorofluorene (824.7 g, 4.48 mol) was dissolved in pyridine (4 L) and stirred. A 40% solution of Triton B (100 mL of benzyltrimethylammonium hydroxide 40% in pyridine according to a general procedure of U. Sprinzak, J. Amer. Chem. Soc. 80 (1958) 5449) was added and oxygen was bubbled into the vigorously stirred solution. This exothermic reaction was run for 20 hours whereupon an additional portion of the Triton B solution (50 mL) was added with continued stirring and oxygen addition for an additional 24 hours. The resulting dark green reaction mixture was treated with Norite (100 g, neutralized charcoal), stirred for 30 minutes and filtered through a Celite pad (diatomaceous earth filter aid). The filter pad was then washed with pyridine (1 L). The combined filtrates were concentrated to a small volume in vacuo with heat. A 5% solution of hydrochloric acid in water (1 L) was added and the pyridine was azeotrophed in vacuo with heat. This process was repeated until a total of 6-8 L of water were evaporated. The granular product was filtered and washed with water (4 L) and air dried. The yellow-orange product was distilled through a large bore short path distillation apparatus (bp 167°-170° C.; 1.5 mm Hg) to yield into a chilled receiving flask the bright yellow 2-fluoro-9-fluorenone (600 g) with a m.p. 113°-115° C. and m/e+. 198 for C13H7FO.

후처리

  1. addition80 (1958) 5449) was added
  2. customoxygen was bubbled into the vigorously stirred solution
  3. customThis exothermic reaction
  4. additionwas added
  5. stirringwith continued stirring
  6. stirringstirred for 30 minutes
  7. filtrationfiltered through a Celite pad (diatomaceous earth filter aid)
  8. washThe filter pad was then washed with pyridine (1 L)
  9. concentrationThe combined filtrates were concentrated to a small volume in vacuo
  10. temperaturewith heat
  11. additionA 5% solution of hydrochloric acid in water (1 L) was added
  12. temperaturewith heat
  13. customwere evaporated
  14. filtrationThe granular product was filtered
  15. washwashed with water (4 L) and air
  16. customdried
  17. distillationThe yellow-orange product was distilled through
  18. distillationpath distillation apparatus (bp 167°-170° C.; 1.5 mm Hg)

출처 및 근거

ORD 기록
ord-710d52f9d5f14f46b865fa466ffac0f8
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04438272

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