Sodium Hydroxide → 4-Cyano-2-methylbenzoic acid

HRID 238395Notes

Reaction equation

HRID 238395 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([CH3:13])[CH:4]=1)#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:13])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18766060Methyl 4-cyano-2-methylbenzoate

Product 1

HCID 118193394-Cyano-2-methylbenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of A-3 (methyl 4-cyano-2-methylbenzoate) (38 g, 0.217 mol) in ethanol (450 mL) was added aqueous sodium hydroxide solution (150 mL, 2.9 M), and the mixture was stirred at room temperature for 12 h. Most of ethanol was removed under reduced pressure, and the residue was diluted with water (300 mL). The aqueous layer was washed with ethyl ether (200 mL×2), and the aqueous layer was acidified with hydrochloric acid (450 mL, 1 M) under 0° C. to pH<6. The mixture was extracted with ethyl acetate (400 mL×3), and the organic layer was washed with brine, dried, and evaporated to give A-4 (4-cyano-2-methylbenzoic acid) (40 g, yield 100%) as a yellow solid.

Workup

  1. customMost of ethanol was removed under reduced pressure
  2. additionthe residue was diluted with water (300 mL)
  3. washThe aqueous layer was washed with ethyl ether (200 mL×2)
  4. customwas acidified with hydrochloric acid (450 mL, 1 M) under 0° C. to pH<6
  5. extractionThe mixture was extracted with ethyl acetate (400 mL×3)
  6. washthe organic layer was washed with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-60e84a9125af41319ed733d6dd36b0b2
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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