Acetone → 3-Iodo-5-(methoxycarbonyl)benzoic acid

HRID 732533Notes

Reaction equation

HRID 732533 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[OH-].[Na+].[CH3:16]C(C)=O.O>CO>[CH3:16][O:12][C:11](=[O:13])[C:4]1[CH:3]=[C:2]([I:1])[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 1039885-Iodoisophthalic acid

Product 1

HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acidYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 5-iodo-isophthalic acid (5 g, 15.6 mmol), NaOH (600 mg, 14.8 mmol) in a mixture of methanol (100 mL), acetone (20 mL) and water (2 mL). Stir at room temperature overnight. Concentrate and redissolve the residue in diethyl ether (100 mL) and water (100 mL). Separate the aqueous layer and wash with diethyl ether (50 mL). Acidify the washed solution with 5 N HCl to about pH=1. Stir for 30 min at room temperature and filter off solid. Wash the solid with water and dry to give the title compound (3.7 g, 77%).

Workup

  1. concentrationConcentrate
  2. dissolutionredissolve the residue in diethyl ether (100 mL)
  3. customSeparate the aqueous layer
  4. washwash with diethyl ether (50 mL)
  5. stirringStir for 30 min at room temperature
  6. filtrationfilter off solid
  7. washWash the solid with water
  8. customdry

Sources & evidence

ORD record
ord-3eabdc3df8cd4ea09f3e4161c4e3451d
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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