Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 1-(2-chloroethoxy)-3-nitrobenzene

HRID 2232318Notes

Reaction equation

HRID 2232318 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:17][CH2:18][CH2:19]OS(C1C=CC(C)=CC=1)(=O)=O>CC(=O)CC>[Cl:17][CH2:18][CH2:19][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 43044241-(2-chloroethoxy)-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 6.96 g. of m-nitrophenol, 100 ml. of 2-butanone, 6.9 g. of potassium carbonate, and 11.74 g. of 2 chloroethyl-tosylate was stirred and heated under reflux for 24 hours. After cooling to room temperature, the salts were filtered off and the filtrate concentrated under vacuum. The residue crystallized on seeding and was recrystallized from carbon tetrachloride to give 8.3 g. of product, m.p. 54.5°-57° C.

Workup

  1. additionA mixture of 6.96 g
  2. temperatureheated
  3. temperatureunder reflux for 24 hours
  4. filtrationthe salts were filtered off
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe residue crystallized on seeding
  7. customwas recrystallized from carbon tetrachloride
  8. customto give 8.3 g

Sources & evidence

ORD record
ord-e7eec975577a49738e06e58d397b4c33
Source dataset
uspto-grants-1988_11
Patent number
US04788195

Reaction notes

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