4-Hydroxybenzenesulfonic acid → 1,2-Bis-(4-sulphophenoxy)-3,3,4,4,5,5-hexafluorocyclopent-1-ene

HRID 981368

반응식

HRID 981368 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N([CH2:17][CH3:18])CC)C.F[C:20]1[C:24]([F:26])([F:25])[C:23]([F:28])([F:27])[C:22]([F:30])([F:29])[C:21]=1F.C(Cl)Cl.CN(C)[CH:37]=[O:38]>O>[S:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][C:20]2[C:24]([F:26])([F:25])[C:23]([F:28])([F:27])[C:22]([F:30])([F:29])[C:21]=2[O:38][C:37]2[CH:18]=[CH:17][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:3][CH:4]=1)([OH:11])(=[O:9])=[O:10]

참가 물질

7

반응물 5

HCID 47654-Hydroxybenzenesulfonic acidHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 11212Perfluorocyclopentene

생성물 1

HCID 200720491,2-Bis-(4-sulphophenoxy)-3,3,4,4,5,5-hexafluorocyclopent-1-ene

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

43.2 (0.3 mol) of 4-hydroxybenzenesulphonic acid (as a 65% strength aqueous solution) and 60.6 g (0.6 mol) of triethylamine were initially introduced at 5° C. in 200 ml of dimethylformamide. 31.8 g (0.15 mol) of perfluorocyclopentene were added dropwise in the course of 15 minutes and the mixture was subsequently stirred at 60° C. for 17 hours. 200 ml of methylene chloride were then added, and the reaction mixture was washed with 200 ml of water, then with 200 ml of 10% strength by weight hydrochloric acid and then again with 200 ml of water and dried. After stripping off the solvent on a rotary evaporator, 47.5 g of an oily crystalline residue remained, which was recrystallized from glacial acetic acid. 27.5 g of crystalline product having a melting point of 251° to 255° C. were obtained, which corresponds point of 251° to 255° C. were obtained, which corresponds to 35.3% of theory. A further 35 g of crude product were isolated from the washing water after acidification and concentration. The mass spectrum of the recrystallized material showed a value for m/e of 520 for the molecular ion.

후처리

  1. washthe reaction mixture was washed with 200 ml of water
  2. dry with materialwith 200 ml of 10% strength by weight hydrochloric acid and then again with 200 ml of water and dried
  3. customon a rotary evaporator, 47.5 g of an oily crystalline residue
  4. customwhich was recrystallized from glacial acetic acid
  5. customwere obtained
  6. custompoint of 251° to 255° C.
  7. customwere obtained

출처 및 근거

ORD 기록
ord-218e2e9eaf0c4bfe9f78b0bee6187a18
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990633

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