Acetic Acid → HCID 53825768, compound

HRID 638621Notes

Reaction equation

HRID 638621 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]([O:18]CC)=[O:17])[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.[OH-].[Na+].[Na].C(O)(=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 54075379HCID 54075379, compound

Product 1

HCID 53825768HCID 53825768, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-[3-chloro-4-(imidazol-1-yl-methyl)phenyl]prop-2-enoate (0.5 g) and sodium hydroxide (0.25 g) in water (10 ml) was stirred and heated under reflux for 3 h. The resulting solution of the sodium salt of the acid was acidified to pH 6 with glacial acetic acid, and the mixture was evaporated to dryness. Ethanol (10 ml) was added to the residue, and the mixture was boiled and filtered. Concentration of the filtrate gave a residue which was recrystallised from ethanol/ether, to give 3-[3-chloro-4-(imidazol-1-ylmethyl)phenyl]prop-2-enoic acid, m.p. 227°-229°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. customthe mixture was evaporated to dryness
  4. additionEthanol (10 ml) was added to the residue
  5. filtrationfiltered
  6. customConcentration of the filtrate gave a residue which
  7. customwas recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-9550c2536c31470d9880d4c449766f3c
Source dataset
uspto-grants-1985_12
Patent number
US04562199

Reaction notes

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