2-Chloroethanol → 2-(3-nitrophenoxy)ethanol

HRID 327649Notes

Reaction equation

HRID 327649 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+].C>C(C(C)=O)C.CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][CH2:13][OH:14])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 297MethaneHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 46689272-(3-nitrophenoxy)ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of m-nitrophenol (28 g, 0.2 mole), 2-chloroethanol (53.6 ml, 0.8 mole), and potassium carbonate (110.4 g, 0.8 mole) in 300 ml methyl ethyl ketone was kept at reflux temperature with stirring overnight. The solid was filtered and dissolved in water. The filtrate was concentrated and some wolid was crystallized from 2-propanol/isopropyl ether. This light-brown solid was collected and weighed 22.78 g (62%). The mother liquor was concentrated and redissolved in toluene/ethyl acetate and extracted with the above aqueous solution. The aqueous layer was further extracted with fresh toluene/ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated to give a second crop of 6.46 g (17.6%). The second crop was dissolved in methanol, stirred with charcoal, filtered, evaporated, and crystallized from 2-propanol/isopropyl ether to give a pure sample. The sample was dried under vacuum at room temperature overnight, mp 85°-86° C.

Workup

  1. temperatureat reflux temperature
  2. filtrationThe solid was filtered
  3. dissolutiondissolved in water
  4. concentrationThe filtrate was concentrated
  5. customsome wolid was crystallized from 2-propanol/isopropyl ether
  6. customThis light-brown solid was collected
  7. concentrationThe mother liquor was concentrated
  8. dissolutionredissolved in toluene/ethyl acetate
  9. extractionextracted with the above aqueous solution
  10. extractionThe aqueous layer was further extracted with fresh toluene/ethyl acetate
  11. washThe combined organic layers were washed with water
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customto give a second crop of 6.46 g (17.6%)
  16. filtrationfiltered
  17. customevaporated
  18. customcrystallized from 2-propanol/isopropyl ether
  19. customto give a pure sample
  20. customThe sample was dried under vacuum at room temperature overnight

Sources & evidence

ORD record
ord-f9318754b4fe44c4a41e4b4dd789dcb8
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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