Sodium Hydroxide → 2-Chloro-4-cyanobenzoic acid

HRID 2307372Notes

Reaction equation

HRID 2307372 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-4fc5aaf9b1434ae59cf2b536d34db04c
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

Loading…