Water → HCID 19700277, compound

HRID 861843Notes

Reaction equation

HRID 861843 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([C:21]([F:24])([F:23])[F:22])([OH:20])[C:16]([F:19])([F:18])[F:17])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H-].[Na+].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.[OH2:40]>CN(C=O)C>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([O:8][C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([C:16]([F:17])([F:18])[F:19])([O:20][S:36]([C:33]3[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=3)(=[O:37])=[O:40])[C:21]([F:23])([F:22])[F:24])[CH:10]=2)([C:4]([F:7])([F:6])[F:5])[C:2]([F:25])([F:26])[F:1])(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 699331,3-Benzenedimethanol, .alpha.1,.alpha.1,.alpha.3,.alpha.3-tetrakis(trifluoromethyl)-

Product 1

HCID 19700277HCID 19700277, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.1 g (10 mmol) of 1,3-bis-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethylethyl)-benzene were dissolved in 20 ml of dry DMF, and 0.75 g (25 mmol) of sodium hydride (80% strength dispersion) was added. The clear solution formed was stirred for a further 30 minutes. 5.25 g (25 mmol) of 4-chlorobenzenesulfonyl chloride in 15 ml of DMF were then added dropwise at 10° to 15° C. The mixture was stirred for 48 hours at room temperature and poured into water. The crystalline precipitate was filtered off, rinsed with water and dried. The residue was chromatographed over a silica gel column with methylene chloride. 4.2 g of 1,3-bis-[1-(4-chlorobenzenesulfonyloxy)-2,2,2-trifluoro-1-trifluoromethylethyl]-benzene were obtained (colorless crystals, m.p.: 125° C.).

Workup

  1. customThe clear solution formed
  2. stirringThe mixture was stirred for 48 hours at room temperature
  3. filtrationThe crystalline precipitate was filtered off
  4. washrinsed with water
  5. customdried
  6. customThe residue was chromatographed over a silica gel column with methylene chloride

Sources & evidence

ORD record
ord-2e70b63de2d24afc942a75c069932d66
Source dataset
uspto-grants-1998_02
Patent number
US05716756

Reaction notes

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