Ethyl Acetate → Bis-(4-methylphenyl)4-cyclohexylphenyl sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

HRID 277685

반응식

HRID 277685 반응식
[C:1]1([CH3:16])[C:2]([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2C)=O)=[CH:3][CH:4]=CC=1.[CH:17]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:43]S(O)(=O)=O.[F:48][C:49]([F:60])([F:59])[CH:50]([F:58])[C:51]([F:57])([F:56])[S:52]([OH:55])(=[O:54])=[O:53].C(O[CH2:65][CH3:66])(=O)C>O>[F:60][C:49]([F:48])([F:59])[CH:50]([F:58])[C:51]([F:56])([F:57])[S:52]([O-:55])(=[O:53])=[O:54].[CH3:43][C:12]1[CH:11]=[CH:10][C:9]([S+:7]([C:2]2[CH:1]=[CH:16][C:65]([CH3:66])=[CH:4][CH:3]=2)[C:26]2[CH:25]=[CH:24][C:23]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)=[CH:28][CH:27]=2)=[CH:14][CH:13]=1

참가 물질

7

반응물 5

HCID 8857Ethyl AcetateHCID 13229CyclohexylbenzeneHCID 586818o-Tolyl sulfoxideHCID 97946281-Propanesulfonic acid, 1,1,2,3,3,3-hexafluoro-HCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

생성물 1

HCID 86757891Bis-(4-methylphenyl)4-cyclohexylphenyl sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

A mixture of 10.36 g (4.5 mmol) of ditolyl sulfoxide with 7.21 g (4.5 mmol) of 4-cyclohexylbenzene was placed in a 125 ml flask. Then 20 ml of a previously prepared phosphorus pentaoxide/metanesulfonic acid reagent (prepared by dissolving 36 g of phosphorus pentaoxide in 360 g of methanesulfonic acid) was added thereto while stirring with a magnetic stirrer. The mixture was heated to about 50° C. Thus, a dark brown solution was obtained. After the exothermic reaction ceased, the mixture was stirred at 45° C. for additional 3 hours. The temperature was then returned to room temperature, and the mixture was poured into 100 ml of water and 100 g of ice. The slightly suspended solution was filtered, followed by addition of 10.44 g (4.5 mmol) of 3,3,3,2,1,1-hexafluoropropane sulfonic acid to yield a white oil. The oil was stirred for 1 hour, and 200 ml of ethyl acetate was added thereto. The mixture was extracted. The organic phase was washed several times with water, and then dried. The solvent was removed by distillation. The oily residue was recrystallized from ethyl acetate and diethyl ether to give 11.5 g of the contemplated material. The structure was confirmed by 1H-NMR (CDCl3) with δ=1.08-1.74 (m, 10H), 2.41-2.43 (m, 7H), 5.27-5.48 (d[m], 1H), 7.16-7.19 (d, 2H), 7.43-7.46 (d, 4H), 7.50-7.53 (d, 4H), and 7.78-7.80 ppm (d, 2H).

후처리

  1. customwas placed in a 125 ml flask
  2. customThus, a dark brown solution was obtained
  3. customAfter the exothermic reaction
  4. stirringthe mixture was stirred at 45° C. for additional 3 hours
  5. customwas then returned to room temperature
  6. filtrationThe slightly suspended solution was filtered
  7. customto yield a white oil
  8. stirringThe oil was stirred for 1 hour
  9. extractionThe mixture was extracted
  10. washThe organic phase was washed several times with water
  11. customdried
  12. customThe solvent was removed by distillation
  13. customThe oily residue was recrystallized from ethyl acetate and diethyl ether

출처 및 근거

ORD 기록
ord-909517338d514dda8ad8e3b254765010
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358665B1

연결된 노트

불러오는 중…