Lithium Hydroxide → 3-Chloro-2-cyanobenzoic acid

HRID 1889053Notes

Reaction equation

HRID 1889053 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[C:5]([C:15]#[N:16])=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9]CC)=[O:8]>O1CCOCC1.O>[Cl:3][C:4]1[C:5]([C:15]#[N:16])=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 14696600Ethyl 3-chloro-2-cyanobenzoate

Product 1

HCID 533972953-Chloro-2-cyanobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide (44.0 mg, 1.049 mmol) was added to a solution of the ethyl 3-chloro-2-cyanobenzoate (200 mg, 0.954 mmol) in 1,4-dioxane (2 mL) and water (2.000 mL) and the reaction was stirred at room temperature for 18 h. LCMS: No SM remains. The solvent was evaporated and the residue was dissolved in water. This was washed with Et2O and then carefully acidified (2M HCl) to pH ˜1. The resulting pink solid was collected, washed with water and dried invacuo to afford desired product in 153 mg).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. washThis was washed with Et2O
  4. customThe resulting pink solid was collected
  5. washwashed with water
  6. customdried invacuo

Sources & evidence

ORD record
ord-289f32184f94463aaab9fc6cb99996d8
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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