Methyl iodide → 2-Chloro-4-methoxybenzoic acid

HRID 1159026Notes

Reaction equation

HRID 1159026 reaction equation
O.[Cl:2][C:3]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].I[CH3:14].[H-].[Na+]>CN(C)C=O>[Cl:2][C:3]1[CH:11]=[C:10]([O:12][CH3:14])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 533954432-Chloro-4-hydroxybenzoic acid hydrate

Product 1

HCID 126480262-Chloro-4-methoxybenzoic acidYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-hydroxybenzoic acid hydrate (2.0 g, 12 mmol), iodomethane (2.9 mL, 46 mmol) and N,N-dimethylformamide (50 mL) was added sodium hydride (1.9 g, 46 mmol; 60% dispersion in mineral oil) in one portion. After stirring the mixture vigorously for 16 h, the reaction was quenched with water and washed with ethyl acetate. The aqueous layer was then acidified with aqueous hydrogen chloride (6N) to give a white precipitate. The mixture was filtered, washed with water, and the filter cake was dried in a vacuum oven to give the desired acid as an off-white solid (1.4 g, 65%). MS (ESI) 187.1, 189.1 (M+H).

Workup

  1. customthe reaction was quenched with water
  2. washwashed with ethyl acetate
  3. customto give a white precipitate
  4. filtrationThe mixture was filtered
  5. washwashed with water
  6. customthe filter cake was dried in a vacuum oven

Sources & evidence

ORD record
ord-9d2bb7f35bad41ca9e46101cb5ba2779
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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