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

HRID 2384064Notes

Reaction equation

HRID 2384064 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 224975Dimethyl 5-chloroisophthalate

Product 1

HCID 247289213-Chloro-5-(methoxycarbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-chloroisophthalic acid dimethyl ester (457 mg, 2 mmol) in methanol (10 mL) is added aqueous 1M NaOH (1.0 mL, 0.65 mmol) and the mixture is stirred at room temperature for 18 hours. The solvent is removed under reduced pressure and water is added to the residue. The solution is washed with ethyl acetate and the aqueous phase is acidified with aqueous 1M HCl. The mixture is extracted with ethyl acetate and the organic phase is washed with brine and dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound. MS 213.2 (M−1); 1H-NMR (400 MHz, DMSO-d6); δ ppm 3.91 (s, 3H), 8.15 (s, 2H), 8.38 (s, 1H), 13.71 (s, 1H).

Workup

  1. customThe solvent is removed under reduced pressure and water
  2. additionis added to the residue
  3. washThe solution is washed with ethyl acetate
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe organic phase is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-24a4238931e049d89d577cebb22a0de6
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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