Phosphorus pentachloride → 4-Toluenesulfonyl chloride

HRID 389005

Reaction equation

HRID 389005 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Na+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O-])(=[O:16])=[O:15])=[CH:10][CH:9]=1>O>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([Cl:2])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 3720192Sodium 4-methylbenzenesulfonate

Product 1

HCID 73974-Toluenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

PCl5 (0.44 mol, 89.2 g) was added to p-toluenesulfonic acid sodium salt (0.4 mmol, 77.6 g). After mixed completely, the mixture was heated to 80° C. in water bath and stirred for 2 h, then cooled to room temperature. The reaction was quenched by pouring onto 600 mL of water and ice. The mixture was filtered and gives the product as white solid. (69.8 g, 90%).

Workup

  1. additionAfter mixed completely
  2. customThe reaction was quenched
  3. additionby pouring onto 600 mL of water and ice
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-38b072c90f144432bf3a3dddf78d0f29
Source dataset
uspto-grants-2013_02
Patent number
US08378058B2

Linked notes

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