Ethanol → 2-(1H-imidazol-1-yl)-1-phenylethanol

HRID 1649392Notes

Reaction equation

HRID 1649392 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)C.[CH2:9]1[O:17][CH:10]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OC(C)C)(C)C>O.N1C=CC=CC=1>[OH:17][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 702EthanolHCID 795ImidazoleHCID 7276Styrene OxideHCID 7914Diisopropyl Ether

Product 1

HCID 322392-(1H-imidazol-1-yl)-1-phenylethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of imidazole (47.0 g, 0.69 mol) in `super-dry` ethanol (175 ml) containing dry pyridine (3.0 ml) was stirred and heated to 75° when styrene oxide (80.0 g, 0.67 mol) was added dropwise at such a rate that the temperature of the reaction mixture was maintained at 80°-85°. Following the addition, the reaction mixture was stirred until the internal temperature had fallen to 50°. Isopropyl ether (300 ml) was then added to the reaction mixture, and the resulting mixture was poured into iced-water (1,000 ml). Separation of the resulting solid by filtration afforded the product which was washed with acetone (1×500 ml) and with ether (2×300 ml), to give 1-(2-hydroxy-2-phenylethyl)imidazole, m.p. 149°-151°.

Workup

  1. additionwas added dropwise at such a rate that the temperature of the reaction mixture
  2. temperaturewas maintained at 80°-85°
  3. additionthe addition
  4. stirringthe reaction mixture was stirred until the internal temperature
  5. customhad fallen to 50°
  6. customSeparation of the resulting solid
  7. filtrationby filtration
  8. customafforded the product which
  9. washwas washed with acetone (1×500 ml) and with ether (2×300 ml)

Sources & evidence

ORD record
ord-3bcb113b53b94b6b9409249cadeeb922
Source dataset
uspto-grants-1983_11
Patent number
US04416895

Reaction notes

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