Triphenylsulfonium chloride → HCID 18544842, compound

HRID 1266946Notes

Reaction equation

HRID 1266946 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:20]([O-:23])(=[O:22])=[O:21])[CH:6]=[CH:7][C:8]=1[O:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[Na+].[Cl-].[C:26]1([S+:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:20]([O-:23])(=[O:21])=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)(=[O:11])=[O:12].[C:39]1([S+:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 61343Triphenylsulfonium chlorideHCID 23712165HCID 23712165, compound

Product 1

HCID 18544842HCID 18544842, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The sodium 3-methoxy-4-(4′-methylphenylsulfonyloxy)-benzenesulfonate crude product obtained in Synthesis Example 1, 90 g, was added to the aqueous triphenylsulfonium chloride solution obtained in Synthesis Example 2 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, 150 g, was purified by silica gel column chromatography (eluent, dichloromethane/methanol), obtaining the end product, triphenylsulfonium 3-methoxy-4-(4′-methylphenyl-sulfonyloxy)benzenesulfonate as an oily matter in an amount of 69 g (yield 56%).

Workup

  1. customThe organic layer was separated
  2. washwashed with 400 g of water
  3. concentrationconcentrated in vacuum
  4. customThe residue, 150 g, was purified by silica gel column chromatography (eluent, dichloromethane/methanol)

Sources & evidence

ORD record
ord-fa2c7b0be44b4d69909bbd8d7c65606c
Source dataset
uspto-grants-2003_04
Patent number
US06551758B2

Reaction notes

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