Water → 3-Cyano-5-(trifluoromethyl)benzoic acid

HRID 878156Notes

Reaction equation

HRID 878156 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]#[N:15])[CH:5]=1.O.O.[OH-].[Li+]>O1CCOCC1>[C:14]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=1)[C:3]([OH:16])=[O:2])#[N:15]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 58902345Methyl 3-cyano-5-(trifluoromethyl)benzoate

Product 1

HCID 589022873-Cyano-5-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-cyano-5-trifluoromethyl-benzoic acid methyl ester (0.084 g, 0.367 mmol) in dioxane (0.5 mL) was added water (0.5 mL) and lithium hydroxide monohydrate (19.2 mg, 0.458 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was evaporated, the residue was taken up in dioxane and 10% aqueous citric acid solution and the layers were separated. The aqueous layer was extracted twice with EtOAc and the organic layers were washed with brine, dried over MgSO4, filtered and evaporated. Light brown solid (0.09 g; 98%). MS (ESI): m/z=214.01 [M−H]−.

Workup

  1. customThe reaction mixture was evaporated
  2. custom10% aqueous citric acid solution and the layers were separated
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. washthe organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d216cebcf6d54d9caed1eb90898e9f41
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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