Ethylene Glycol → 2-Methyl-4-(trifluoromethyl)benzoic acid
Reaction equation
[OH-:1].[K+].[CH3:3][C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8]C=1C#N.[CH2:16]([OH:19])[CH2:17]O>O>[CH3:3][C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:17]=1[C:16]([OH:19])=[O:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 125 °C
Procedure
Potassium hydroxide (15.7 g, 0.28 mole) and 15 mL of water were added as a solution to a stirred, heterogeneous mixture of 2-methyl-4-(trifluoromethyl)benzonitrile (13 g, 70 mmol) and 135 mL of ethylene glycol. The reaction mixture was heated at 120-130° C. for 20 hours and allowed to cool to room temperature. The dark solution was poured into 800 mL of water and filtered through celite. The filtrate was washed with ether and then the aqueous was acidified with concentrated hydrochloric acid. This aqueous phase was extracted three times with ethyl acetate, the organic extracts were combined, dried over magnesium sulfate and evaporated under reduced pressure to afford the title compound as a tan solid.
Workup
- temperatureto cool to room temperature
- filtrationfiltered through celite
- washThe filtrate was washed with ether
- extractionThis aqueous phase was extracted three times with ethyl acetate
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-481f26774a1a4708aca3ea7870e9843d
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07338978B2
Reaction notes
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