4-Toluenesulfonyl chloride → Acetonitrile, 2-(((4-methylphenyl)sulfonyl)oxy)-

HRID 437177

Reaction equation

HRID 437177 reaction equation
[C:1](#[N:4])[CH2:2][OH:3].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1.COCCOC.[OH-].[Na+]>O>[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11]([O:3][CH2:2][C:1]#[N:4])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7857HydroxyacetonitrileHCID 80711,2-DimethoxyethaneHCID 14798Sodium Hydroxide

Product 1

HCID 84525Acetonitrile, 2-(((4-methylphenyl)sulfonyl)oxy)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Method of preparation: 8.1 g (0.1 mole of glycolonitrile (70% aqueous solution) is added to a cooled (15° -20° C.) mixture of 9.5 g (0.05 mole) of p-toluenesulfonyl chloride in 20 ml. of 1,2-dimethoxyethane and 50 ml. distilled water. A solution of 2.1 g (0.05 mole) of NaOH in 50 ml. distilled water is added slowly with stirring at 20°-25° C. over a period of 6.5 hours, maintaining the pH of the reaction mixture at about 8. The insoluble material is filtered off, washed with cold water, and dried at 40° C. under vacuum to yield 6.8 g (64% conversion) of the product, a light brown solid, m.p. 48°-50.5° C.

Workup

  1. customMethod of preparation
  2. temperaturea cooled
  3. temperaturemaintaining the pH of the reaction mixture at about 8
  4. filtrationThe insoluble material is filtered off
  5. washwashed with cold water
  6. customdried at 40° C. under vacuum
  7. customto yield 6.8 g (64% conversion) of the product

Sources & evidence

ORD record
ord-d7f52cd9c8264487915d7e6f4520eb50
Source dataset
uspto-grants-1977_06
Patent number
US04029809

Linked notes

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