Sodium Hydroxide → 4-Iodo-2-methoxybenzoic acid

HRID 1830077Notes

Reaction equation

HRID 1830077 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:5]=1[O:11][CH3:12].[OH-].[Na+]>O1CCCC1>[I:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:13])=[O:2])=[C:5]([O:11][CH3:12])[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22619468Benzoic acid, 4-iodo-2-methoxy-, methyl ester

Product 1

HCID 134507564-Iodo-2-methoxybenzoic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 4-iodo-2-methoxybenzoic acid methyl ester of Step A (2.7 g, 9.24 mmol) was dissolved in tetrahydrofuran (40 mL) and 1 N sodium hydroxide (20 mL, 20 mmol) was added. The reaction mixture was heated at reflux for 3 hours, then cooled and concentrated in vacuo to give an orange oil that was partitioned between ethyl acetate and 2 N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 2.5 g of title product as a yellow-orange solid, m.p. 144–146° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto give an orange oil that
  6. customwas partitioned between ethyl acetate and 2 N hydrochloric acid
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90525c054a8648908e59a0cdde8a5e83
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

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