Sodium Hydroxide → 5-Chloro-4-iodo-2-methoxybenzoic acid

HRID 489574Notes

Reaction equation

HRID 489574 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([I:11])=[CH:6][C:5]=1[O:12][CH3:13].[OH-].[Na+]>CO>[Cl:10][C:8]1[C:7]([I:11])=[CH:6][C:5]([O:12][CH3:13])=[C:4]([CH:9]=1)[C:3]([OH:14])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69314795Methyl 5-chloro-4-iodo-2-methoxybenzoate

Product 1

HCID 167918585-Chloro-4-iodo-2-methoxybenzoic acidYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture od 5-chloro-4-iodo-2-methoxy benzoic acid methyl ester of Step B (3.00 g, 9.19 mmol) and sodium hydroxide (1.10 g, 27.6 mmol) in methanol (92 mL) was refluxed for 12 hours. The reaction was cooled to room temperature and the solvent evaporated. The residue was dissolved in 1 N sodium hydroxide (75 mL), the solution washed with diethyl ether and the organic washings discarded. The aqueous phase was acidified with 2 N hydrochloric acid and extracted with diethyl ether. The combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated to afford the title carboxylic acid (2.64 g) as orange crystals, m.p. 150-151° C.

Workup

  1. customthe solvent evaporated
  2. dissolutionThe residue was dissolved in 1 N sodium hydroxide (75 mL)
  3. washthe solution washed with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a2605aa8c4554696a50e2bf9787bb745
Source dataset
uspto-grants-2005_12
Patent number
US06977254B2

Reaction notes

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