Iodine → 3-Chloro-5-hydroxybenzoic Acid

HRID 1990726Notes

Reaction equation

HRID 1990726 reaction equation
II.[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:13]C)[CH:12]=1)[C:7]([OH:9])=[O:8]>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([OH:13])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 807IodineHCID 129093413-Chloro-5-methoxybenzoic acid

Product 1

HCID 130716463-Chloro-5-hydroxybenzoic AcidYield 83.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent2×

Procedure

Alumina (1.65 g, 60 mmol) and iodine (21 g, 82 mmol) were refluxed in toluene (200 mL) for 2 hours. Then, 3-chloro-5-methoxybenzoic acid (11.2 g, 60.2 mmol; see step (i) above) dissolved in toluene (50 mL) was added, together with tetrabutylammonium iodide (1.5 g, 4 mmol), and the mixture was refluxed for another 2 hours. After cooling to ambient temperature, extractive work up gave 8.7 g, 50 mmol (yield: 83%) of the sub-title compound.

Workup

  1. temperaturethe mixture was refluxed for another 2 hours

Sources & evidence

ORD record
ord-c96a069d0d8c44788d36421119196dec
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

Loading…