p-Toluenesulfonic acid → Triphenylsulfonium p-toluenesulfonate

HRID 2916

반응식

HRID 2916 반응식
[Br-].[C:2]1([S+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1>O>[S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)([O-:30])(=[O:29])=[O:28].[C:15]1([S+:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 11984010Triphenylsulfonium Bromide

생성물 1

HCID 21872467Triphenylsulfonium p-toluenesulfonate수율 73.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of triphenylsulfonium bromide (6.87 g, 20.0 mmol) and p-toluenesulfonic acid (3.80 g, 20.0 mmol) in water (100 ml) was heated at a gentle reflux for 15 hours under nitrogen. After cooling to room temperature, the clear solution was extracted with dichloromethane (4×75 ml). The combined organic extracts were washed with water until neutral (4×75 ml) and dried (MgSO4 ). The solvent was removed under reduced pressure and the residue dried by heating at 80° C. in vacuo for 36 hours to give a crude onium salt as a off-white solid (6.35 g). Recrystallization from acetone-ethyl acetate gave triphenylsulfonium rosylate as a white crystalline solid (5.72 g, 66%).

후처리

  1. temperaturea gentle reflux for 15 hours under nitrogen
  2. extractionthe clear solution was extracted with dichloromethane (4×75 ml)
  3. washThe combined organic extracts were washed with water until neutral (4×75 ml)
  4. dry with materialdried (MgSO4 )
  5. customThe solvent was removed under reduced pressure
  6. customthe residue dried
  7. temperatureby heating at 80° C. in vacuo for 36 hours

출처 및 근거

ORD 기록
ord-859a3ba4fca04957adca8f06dc6bef2a
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731364

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