Hydrogen iodide → 2,3-Dichloro-4-(4-hydroxybenzoyl)phenoxyacetic acid

HRID 1439215Notes

Reaction equation

HRID 1439215 reaction equation
C[O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([C:9]2[CH:19]=[CH:18][C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:11]([Cl:20])[C:10]=2[Cl:21])=[O:8])=[CH:5][CH:4]=1.I>CCOCC>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH:19]=[CH:18][C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:11]([Cl:20])[C:10]=2[Cl:21])=[O:8])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 13212600[2,3-Dichloro-4-(4-methoxybenzoyl)phenoxy]acetic acid

Product 1

HCID 128540042,3-Dichloro-4-(4-hydroxybenzoyl)phenoxyacetic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-(4-methoxybenzoyl)-2,3-dichlorophenoxy acetic acid (3.55 g., 0.01 mole) and hydriodic acid (7.5 ml.) was refluxed at 180°-190° C. for 4 hours. The reaction mixture was concentrated and the solid residue was stirred with water for one hour and filtered. The solid obtained was dissolved in ether and dried (MgSO4). The solvent was removed in vacuo and the residue was recrystallized from ether - pet. ether mixture to give 2 g. (60%) of the product; m.p. 218°-219° C.

Workup

  1. temperaturewas refluxed at 180°-190° C. for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. filtrationfiltered
  4. customThe solid obtained
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was recrystallized from ether - pet. ether mixture
  8. customto give 2 g

Sources & evidence

ORD record
ord-8d4e3f189ac246cbb6c36c7ab9e2e64e
Source dataset
uspto-grants-1977_11
Patent number
US04058559

Reaction notes

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