4-Toluenesulfonyl chloride → HCID 13955194, compound

HRID 1463600Notes

Reaction equation

HRID 1463600 reaction equation
[CH2:1]([O:3][CH:4]([CH3:7])[CH2:5][OH:6])[CH3:2].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:6][CH2:5][CH:4]([O:3][CH2:1][CH3:2])[CH3:7])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 294202-Ethoxy-1-propanol

Product 1

HCID 13955194HCID 13955194, compound

Procedure

20.8 g (0.20 mol) of 2-ethoxypropanol are added slowly during 20 minutes with stirring to a mixture of 43.3 g (0.227 mol) of toluene-p-sulphonylchloride and 20 ml of dry pryridine. The temperature of the reaction mixture is kept at 20° with external cooling. After stirring for 2 hours at 20°, the mixture is poured into ice-water and extracted with ether. The ether layer is washed with 2N sulphuric acid, with water and with saturated sodium hydrogencarbonate solution. After drying over sodium sulphate, filtration and evaporation in vacuo, 2-ethoxypropyl toluene-p-sulphonate is obtained as a yellow oil.

Workup

  1. customis kept at 20° with external cooling
  2. extractionextracted with ether
  3. washThe ether layer is washed with 2N sulphuric acid, with water and with saturated sodium hydrogencarbonate solution
  4. dry with materialAfter drying over sodium sulphate, filtration and evaporation in vacuo

Sources & evidence

ORD record
ord-cb85dc99d6d946a7855716fb226177ad
Source dataset
uspto-grants-1994_04
Patent number
US05300679

Reaction notes

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