Water → phenyl 2,4,6-trimethylbenzenesulfonate

HRID 1031847Notes

Reaction equation

HRID 1031847 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[S:19](Cl)(=[O:21])=[O:20]>C1(C)C=CC=CC=1>[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[S:19]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:20])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 130462-Mesitylenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 230708phenyl 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.4 g of phenol is added to a mixture containing 9.17 g of 48% NaOH, 50 ml of water and 50 ml of toluene. To the resulting mixture is added 22.9 g of mesitylenesulfonyl chloride, and reaction is carried out at 60° to 65° C. for 1 hour. After separating the aqueous layer, toluene is removed from the toluene layer by distillation. The resulting desired compound is purified with methanol.

Workup

  1. additionTo the resulting mixture is added
  2. customAfter separating the aqueous layer, toluene
  3. customis removed from the toluene layer by distillation
  4. customThe resulting desired compound is purified with methanol

Sources & evidence

ORD record
ord-f9c2d5d79ae942d6bc09f9876e47b089
Source dataset
uspto-grants-1990_09
Patent number
US04956333

Reaction notes

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