4-Toluenesulfonyl chloride → HCID 13955194, compound

HRID 973607Notes

Reaction equation

HRID 973607 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 cooling for 2 hours at 20°, the mixture is poured into ice-water and extracted with ether. The ether layer is washed with 2 N 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. A solution of 51.5 g (0.199 mol) of 2-ethoxypropyl toluene-p-sulphonate and 36.5 g (0.243 mol) of sodium iodide in 250 ml of acetone is stirred under reflux for 2 hours. After cooling to 10°, the separated sodium toluene-p-sulphonate is removed by filtration, and the solvent is evaporated through a 15 cm Vigreux-column at atmospheric pressure. The crude product is dissolved in ether and washed with a 10% (b.w.) solution of sodium thiosulphate. Drying over sodium sulphate, filtration and evaporation of the solvent through a 15 cm Vigreux column, followed by fractional distillation yields 3-ethoxypropyliodide, b.p. 97°/40 mbar.

Workup

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

Sources & evidence

ORD record
ord-51c6e12869e94c66b9281d3426d5e4de
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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