Triphenylsulfonium chloride → HCID 18469754, compound

HRID 2228367Notes

Reaction equation

HRID 2228367 reaction equation
[C:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[C:19]1([S+:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[C:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([O-:17])(=[O:15])=[O:16])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:32]1([S+:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 61343Triphenylsulfonium chlorideHCID 18469740HCID 18469740, compound

Product 1

HCID 18469754HCID 18469754, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-phenylmethylbenzenesulfonic acid crude product obtained in Synthesis Example 1 was added to the aqueous triphenylsulfonium chloride solution obtained in Synthesis Example 2 and 90 g of dichloromethane, which was stirred for one hour at room temperature. The organic layer was separated, washed with 100 g of water, and evaporated in vacuum. The residue, 27 g, was purified by silica gel column chromatography (eluent, dichloromethane/methanol), obtaining the end product, triphenylsulfonium 4-phenylmethylbenzenesulfonate. It was 21 g (yield 52%) of an oily matter containing a minor amount of solvents (methanol, etc.).

Workup

  1. customThe organic layer was separated
  2. washwashed with 100 g of water
  3. customevaporated in vacuum
  4. customThe residue, 27 g, was purified by silica gel column chromatography (eluent, dichloromethane/methanol)

Sources & evidence

ORD record
ord-d0a27f17fca4480caf5f5daaf7dce84c
Source dataset
uspto-grants-2002_07
Patent number
US06416928B1

Reaction notes

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