Hydrogen iodide → HCID 13066682, compound

HRID 1164007Notes

Reaction equation

HRID 1164007 reaction equation
I.C[O:3][C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([OH:21])=[O:20].S([O-])(O)=O.[Na+]>C(OC(=O)C)(=O)C>[OH:3][C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 20513509HCID 20513509, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13066682HCID 13066682, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

48% Hydriodic acid (40 ml) was added dropwise to a solution of 2-[2-methoxy-3-(4-chlorophenoxy)phenyl]acetic acid (6.7 g) in acetic anhydride (20 ml) with stirring under ice-cooling in 5 minutes, and the mixture was refluxed under heating for 20 minutes. The reaction mixture was poured into an ice-water containing a small amount of sodium hydrogen sulfite and allowed to stand. The precipitating crystals were collected by filtration, washed with water, dried and then recrystallized from a mixture of benzene and n-hexane to give 2-[2-hydroxy-3-(4-chlorophenoxy)phenyl]acetic acid (4.4 g). mp 100°-102° C.

Workup

  1. temperaturecooling in 5 minutes
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 20 minutes
  4. filtrationThe precipitating crystals were collected by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-a310617d209f495e937af5e356c4f60a
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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