Water → HCID 19700289, compound

HRID 861842Notes

Reaction equation

HRID 861842 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+].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.[OH2:40]>CN(C=O)C>[F:1][C:2]([F:25])([F:26])[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([C:16]([F:17])([F:18])[F:19])([O:20][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:36])=[O:40])[C:21]([F:23])([F:22])[F:24])[CH:10]=1)([O:8][S:35]([C:32]1[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=1)(=[O:37])=[O:36])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 699331,3-Benzenedimethanol, .alpha.1,.alpha.1,.alpha.3,.alpha.3-tetrakis(trifluoromethyl)-

Product 1

HCID 19700289HCID 19700289, 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. 4.75 g (25 mmol) of toluene-4-sulfonyl chloride in 15 ml of DMF were 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, washed with water and dried. The residue was chromatographed over a silica gel column with methylene chloride. 3.5 g of 1,3-bis-[2,2,2-trifluoro-1-(toluene-4-sulfonyloxy)-1-trifluoromethylethyl]-benzene were obtained (colorless crystals, m.p.: 131° 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. washwashed with water
  5. customdried
  6. customThe residue was chromatographed over a silica gel column with methylene chloride

Sources & evidence

ORD record
ord-197c48c460cd48f68ddcc9ea51b4661e
Source dataset
uspto-grants-1998_02
Patent number
US05716756

Reaction notes

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