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

HRID 1432062Notes

Reaction equation

HRID 1432062 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-de2455a8911444ccb5dba5a58f6f61b4
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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