4-Toluenesulfonyl chloride → HCID 13955194, compound

HRID 1612682Notes

Reaction equation

HRID 1612682 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>N1C=CC=CC=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

4

Reactant 2

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

Product 1

HCID 13955194HCID 13955194, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 pyridine. 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-e03689bd3a024d039f56ba3ad0812334
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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