Lithium Hydroxide → 3-Cyano-4-isobutylbenzoic acid

HRID 1942601Notes

Reaction equation

HRID 1942601 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8]C)=[O:7])#[N:2].[Li+].[OH-]>CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59316752Methyl 3-cyano-4-isobutylbenzoate

Product 1

HCID 222281753-Cyano-4-isobutylbenzoic acidYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 3-cyano-4-(2-methylpropyl)benzoate (D23) (800 mg) in methanol (30 mL) and water (5 mL) at room temperature was added LiOH (441 mg). Then the reaction mixture was stirred at 25° C. for 4 h. Methanol was removed under reduced pressure and water (30 mL) was added. 2N HCl was added to the solution until pH=5. After filtration, the solid was dried to give 3-cyano-4-(2-methylpropyl)benzoic acid (D24) (735 mg) as a white solid. MS (ES): C12H13NO2 requires 203. found 204.1 (M+H+).

Workup

  1. customMethanol was removed under reduced pressure and water (30 mL)
  2. additionwas added
  3. addition2N HCl was added to the solution until pH=5
  4. filtrationAfter filtration
  5. customthe solid was dried

Sources & evidence

ORD record
ord-b6ed8e9b7a904c7bb5725f6938cecf9c
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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