Sodium Hydroxide → 2-Chloro-4-cyanobenzoic acid

HRID 1635863Notes

Reaction equation

HRID 1635863 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53845357Methyl 2-chloro-4-cyanobenzoate

Product 1

HCID 2318942-Chloro-4-cyanobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-chloro-4-cyanobenzoic acid, methyl ester (24.3 g) in methanol (150 ml) was added 2.5N sodium hydroxide (54.5 ml). After stirring at room temperature. for 45 minutes, the solvent was removed in vacuo. The residue was dissolved in water, cooled in an ice bath, and made acidic with 2N hydrochloric acid (14 ml). The resulting precipitate was filtered and dried in vacuo to yield the title compound as a solid (22.55 g) m.p. 154-158° C.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. temperaturecooled in an ice bath
  4. filtrationThe resulting precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c5a57b9d638e4f359d5f93afa9944ec4
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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