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

HRID 1862805Notes

Reaction equation

HRID 1862805 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
  8. custompet. ether mixture to give 2 g

Sources & evidence

ORD record
ord-fbabffc20a6a49fda3f550b80a3d664c
Source dataset
uspto-grants-1979_09
Patent number
US04166819

Reaction notes

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