Sulfuric Acid → 1-[3-(3-Chloro-4-hydroxyphenyl)propyl]imidazole

HRID 322340Notes

Reaction equation

HRID 322340 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[CH:5]=[CH:6][C:7]=1[O:8]COC.OS(O)(=O)=O.[OH-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 220096291-[3-(3-Chloro-4-methoxymethoxyphenyl)propyl]imidazole

Product 1

HCID 220098751-[3-(3-Chloro-4-hydroxyphenyl)propyl]imidazoleYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-[3-(3-chloro-4-methoxymethoxyphenyl)propyl]imidazole (4.50 g), 10% H2SO4 (50 ml) and acetone (50 ml) was refluxed for 3 h. Sodium hydroxide (7.0 g) was added to the mixture at 0° C., and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated to obtain 1-[3-(3-chloro-4-hydroxyphenyl)propyl]imidazole (3.50 g, 92%). Recrystallization from ethanol gave colorless prisms, 112-113° C.

Workup

  1. temperaturewas refluxed for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5ec0ef61485c442ba082aa29783ca548
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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