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

HRID 1436676Notes

Reaction equation

HRID 1436676 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-02ec796f3bb74212876d4539c5e25da6
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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