Hydrochloric Acid → 2-(Benzyloxy)ethyl 4-methylbenzenesulfonate

HRID 596931Notes

Reaction equation

HRID 596931 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.Cl>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][O:11][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=1)(=[O:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 121412-(Benzyloxy) ethanol

Product 1

HCID 5613752-(Benzyloxy)ethyl 4-methylbenzenesulfonateYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
15 °C

Procedure

In 69.2 g of pyridine was dissolved 33.27 g of 2-benzyloxy-ethanol, and to this solution was then added with stirring 45.9 g of p-tosyl chloride at an inner temperature in the range of 5°- 10° C. The resulting mixture was stirred at a temperature of 15° C for 2 hours. After completion of the reaction, a mixture solution of 130 ml of conc. hydrochloric acid and 450 ml of ice-water was added to the resulting reaction mixture and then subjected to extraction with benzene. The extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. Upon evaporation of the solvent from the extract, there was obtained 66.9 g of 2-benzyloxy-1-(p-toluenesulfonyloxy)ethane as an oil.

Workup

  1. additionto this solution was then added
  2. customAfter completion of the reaction
  3. extractionsubjected to extraction with benzene
  4. washThe extract was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customUpon evaporation of the solvent from the extract

Sources & evidence

ORD record
ord-7d11c8e1b791451d9f1afe8de49f0744
Source dataset
uspto-grants-1977_03
Patent number
US04012429

Reaction notes

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