Sodium Hydroxide → 3-Chloro-5-(methoxycarbonyl)benzoic acid

HRID 917547Notes

Reaction equation

HRID 917547 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C)=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 224975Dimethyl 5-chloroisophthalate

Product 1

HCID 247289213-Chloro-5-(methoxycarbonyl)benzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step N1. A mixture of dimethyl 5-chloroisophthalate (6.84 g, 30 mmol), in methanol (150 mL) was treated with 1M sodium hydroxide (27 mL, 27 mmol) and the reaction stirred at room temperature for 16 hours. The mixture was concentrated under vacuum and the resulting residue was dissolved in water. The mixture was extracted with ethyl acetate three times. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to afford 3-chloro-5-(methoxycarbonyl)benzoic acid (4.8 g, 75%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe resulting residue was dissolved in water
  3. extractionThe mixture was extracted with ethyl acetate three times
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-147df0c3fa8e44d1ba87ba35b55ea2ee
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

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