Sodium Hydroxide → (2-Chloro-4-trifluoromethylphenyl)propynoic acid

HRID 735096Notes

Reaction equation

HRID 735096 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]([O:16]CC)=[O:15].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68818493Ethyl (2-chloro-4-trifluoromethylphenyl)propynoate

Product 1

HCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.65 g (1.175 mmol) of ethyl (2-chloro-4-trifluoromethylphenyl)propynoate is dissolved in 20 mL of ethanol, combined with 2 mL of 2M sodium hydroxide solution, and stirred for 3 hours at ambient temperature. The reaction mixture is evaporated down, the residue is taken up in water, and extracted with ethyl acetate. The aqueous phase is combined with 2 mL of 1M hydrochloric acid and stirred for 1 hour at ambient temperature. Then it is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate. Yield: 0.14 g (48% of theory); C10H4ClF3O2 (M=248.59); calc.: molecular ion peak (M−H)−: 247/249; found: molecular ion peak (M−H)−: 247/249; Rf value: 0.09 (silica gel, petroleum ether/ethyl acetate (4:1)).

Workup

  1. customThe reaction mixture is evaporated down
  2. extractionextracted with ethyl acetate
  3. stirringstirred for 1 hour at ambient temperature
  4. extractionThen it is extracted three times with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate

Sources & evidence

ORD record
ord-254f844c5bb045df879a903bdeb6c714
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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