Lithium Hydroxide → 3-cyano-5-methoxybenzoic acid

HRID 1791345Notes

Reaction equation

HRID 1791345 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([C:12]#[N:13])[CH:5]=1.[OH-].[Li+]>C1COCC1>[C:12]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH3:11])[CH:7]=1)[C:3]([OH:14])=[O:2])#[N:13]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 53419624HCID 53419624, compound

Product 1

HCID 103973283-cyano-5-methoxybenzoic acidYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 3-cyano-5-methoxy-benzoic acid methyl ester (3.4 g, 18.7 mmol) in THF (45 mL) was treated with 0.5 N lithium hydroxide (45 mL, 22.4 mmol). The reaction was stirred at 75° C. for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH 2) by the addition of 1 N HCl. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulfate. After removal of solvent in vacuo, 2.5 g (77%) of 3-cyano-5-methoxybenzoic acid was isolated as a white solid. 1H NMR (DMSO), δ(ppm): 7.86 (s, 1H), 7.71 (m, 2H), 3.87 (s, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. additionby the addition of 1 N HCl
  4. extractionto extract the precipitate, which
  5. washwas then washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of solvent in vacuo

Sources & evidence

ORD record
ord-a4151484a7b049b5ab77f711a10b50be
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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