Lithium Hydroxide → 2-Ethoxy-4-(trifluoromethyl)benzoic acid
Reaction equation
C([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[O:15][CH2:16][CH3:17])C.[Li+].[OH-]>C1COCC1.CO>[CH2:16]([O:15][C:6]1[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:5]=1[C:4]([OH:18])=[O:3])[CH3:17]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Hydroxy-4-trifluoromethyl-benzoic acid (1.20 g, 5.82 mmol) was reacted with ethyliodide (2.2 eq) and K2CO3 (1.69 g) in DMF solution. The reaction mixture was quenched by adding H2O. The mixture was extracted with ethyl acetate (40 ml×3). A combined organic layer was washed sat NaHCO3 solution (30 ml), H2O (40 ml×5), and brine, and then dried over MgSO4. The filterate was concentrated in vacuo to yield 2-ethoxy-4-trifluoromethyl benzoic acid ethyl ester. The ester obtained above was reacted with 1 N LiOH (15 ml) in THF and CH3OH cosolvent for 2 hrs as described above to yield title compound (1.20 g, 88%)
Sources & evidence
- ORD record
- ord-8a1f172a9cbe401b91b5ef256879c430
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557872B2
Reaction notes
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