2-Chloroethanol → 2-[4-(2-Methyl-1H-imidazol-1-yl)phenoxy]ethanol

HRID 327651Notes

Reaction equation

HRID 327651 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.Cl[CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(C(C)=O)C>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:15][CH2:16][OH:17])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 112522894-(2-Methyl-1H-imidazol-1-YL)phenol

Product 1

HCID 191086662-[4-(2-Methyl-1H-imidazol-1-yl)phenoxy]ethanol

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-(2-Methyl-1H-imidazol-1-yl)phenol (10.0g, 0.057 mole), 2-chloroethanol (13.88 g, 0.172 mole) and potassium carbonate (23.74 g, 0.172 mole) were combined in methyl ethyl ketone (200 ml) and heated at reflux temperature for four days. The solution was cooled and the solid filtered and rinsed with acetone. The filtrate was concentrated to a residue and the residue triturated with hot acetone (2×50 ml). The remaining solid (1.5 g) was dissolved in methylene chloride. Insoluble materials were removed by filtrateion, and the filtrate concentraed to obtain 0.50 g (4%), mp 125°-127° C. Proton NMR indicates that methylene chloride is present in the sample.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for four days
  3. temperatureThe solution was cooled
  4. filtrationthe solid filtered
  5. washrinsed with acetone
  6. concentrationThe filtrate was concentrated to a residue
  7. customthe residue triturated with hot acetone (2×50 ml)
  8. dissolutionThe remaining solid (1.5 g) was dissolved in methylene chloride
  9. customInsoluble materials were removed by filtrateion
  10. customto obtain 0.50 g (4%), mp 125°-127° C

Sources & evidence

ORD record
ord-b025a0e5c0284b4b9adfcfef3ea5a35f
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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