Triphenylsulfonium chloride → HCID 23435187, compound

HRID 2120533Notes

Reaction equation

HRID 2120533 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([S:22]([O-:25])(=[O:24])=[O:23])=[CH:14][CH:13]=2)(=[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:3]=[CH:4][C:5]([S:8]([O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([S:22]([O-:25])(=[O:24])=[O:23])=[CH:14][CH:13]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=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 23712170HCID 23712170, compound

Product 1

HCID 23435187HCID 23435187, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The sodium 4-(4′-methylphenylsulfonyloxy)naphthalene-1-sulfonate crude product obtained in Synthesis Example 2, 48 g, was added to one half of the aqueous triphenylsulfonium chloride solution obtained in Synthesis Example 4 and 200 g of dichloromethane, which was stirred for one hour at room temperature. The organic layer was separated, washed with 200 g of water, and concentrated in vacuum. The residue, 60 g, was purified by recrystallization from diethyl ether, obtaining the end product, triphenylsulfonium 4-(4′-methylphenylsulfonyloxy)naphthalene-1-sulfonate as crystals in an amount of 49 g (yield 76%).

Workup

  1. customThe organic layer was separated
  2. washwashed with 200 g of water
  3. concentrationconcentrated in vacuum
  4. customThe residue, 60 g, was purified by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-2d695418e6354faaac3caced887a974e
Source dataset
uspto-grants-2004_02
Patent number
US06692893B2

Reaction notes

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