Triphenylsulfonium chloride → HCID 23435220, compound

HRID 2120532Notes

Reaction equation

HRID 2120532 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([S:22]([O-:25])(=[O:24])=[O:23])[CH:16]=[CH:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Na+].[Cl-].[C:28]1([S+:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([S:22]([O-:25])(=[O:24])=[O:23])[CH:16]=[CH:15]3)(=[O:9])=[O:10])=[CH:4][CH:3]=1.[C:41]1([S+:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 61343Triphenylsulfonium chlorideHCID 23712166HCID 23712166, compound

Product 1

HCID 23435220HCID 23435220, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The sodium 6-(4′-methylphenylsulfonyloxy)naphthalene-2-sulfonate crude product obtained in Synthesis Example 1, 90 g, was added to the aqueous triphenylsulfonium chloride solution obtained in Synthesis Example 4 and 400 g of dichloromethane, which was stirred for one hour at room temperature. The organic layer was separated, washed with 400 g of water, and concentrated in vacuum. The residue, 130 g, was purified by recrystallization from diethyl ether, obtaining the end product, triphenylsulfonium 6-(4′-methylphenylsulfonyloxy)naphthalene-2-sulfonate as crystals in an amount of 100 g (yield 79%).

Workup

  1. customThe organic layer was separated
  2. washwashed with 400 g of water
  3. concentrationconcentrated in vacuum
  4. customThe residue, 130 g, was purified by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-0e91428f159d4e0e9dcc812b0c512568
Source dataset
uspto-grants-2004_02
Patent number
US06692893B2

Reaction notes

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