2-Chloroethanol → Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)

HRID 414474Notes

Reaction equation

HRID 414474 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][CH2:13][CH2:14][OH:15]>N1C=CC=CC=1>[Cl:12][CH2:13][CH2:14][O:15][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 342-ChloroethanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Para-toluenesulphonyl chloride (20.5 g) was added to a mixture of 2-chloroethanol (8.6 g) and pyridine (50 ml). After stirring for one hour at 0° C., the mixture was added to ice and the organic phase was extracted with ether. The extract was washed with dilute hydrochloric acid, dried with magnesium sulphate, and evaporated, to yield 2-chloroethyl-p-toluenesulphonate.

Workup

  1. additionthe mixture was added to ice
  2. extractionthe organic phase was extracted with ether
  3. washThe extract was washed with dilute hydrochloric acid
  4. dry with materialdried with magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-d04ee05aaa994a18ad0e95e10f9b44d8
Source dataset
uspto-grants-1988_12
Patent number
US04792551

Reaction notes

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