2-Chloroethanol → 2-Chloroethyl 2-methylpropane-1-sulfonate

HRID 866287Notes

Reaction equation

HRID 866287 reaction equation
[CH2:1]([Cl:4])[CH2:2][OH:3].CCOCC.[CH2:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]([CH3:13])[CH3:12]>C(N(CC)CC)C>[CH2:10]([S:14]([O:3][CH2:2][CH2:1][Cl:4])(=[O:16])=[O:15])[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 3283Diethyl EtherHCID 1822361-Propanesulfonyl chloride, 2-methyl-

Product 1

HCID 227699422-Chloroethyl 2-methylpropane-1-sulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
23 °C

Procedure

A mixture was formed containing 6.7 ml. of ethylene chlorohydrin, 70 ml. of ether and 15.6 g. of isobutane sulfonyl chloride. Then, 14 ml. of triethylamine was added dropwise to the mixture with stirring in an ice bath over a period of 30 minutes at 12°-14° C. While stirring the mixture was allowed to warm to 23° C. (1 hour) and was then washed with water (100 ml.), dried over magnesium sulfate and evaporated to yield 19.7 g. of a colorless oil. nD30 1.4502.

Workup

  1. customA mixture was formed
  2. additioncontaining 6.7 ml
  3. stirringWhile stirring the mixture
  4. washwas then washed with water (100 ml.)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto yield 19.7 g

Sources & evidence

ORD record
ord-e540f21fa3de434e8e9e6380e144a9ad
Source dataset
uspto-grants-1978_07
Patent number
US04098599

Reaction notes

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