Acetic Acid → 2,4-Bis(trifluoromethyl)phenylacetic acid
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[C:5]#N.OS(O)(=O)=O.O.[C:23]([OH:26])(=[O:25])C>>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[CH2:5][C:23]([OH:26])=[O:25]Participants
5
Conditions
- Temperature
- 120 °C
Procedure
2,4-Bis(trifluoromethyl)benzonitrile (41.5 mmol, 10.51 g) was taken up in 100 mL acetic acid, 50 mL conc. H2SO4, and 20 mL water. This was heated to 120° C. for 3 h. The reaction was then diluted with 1 L ice water, and extracted with 2×300 mL ethyl acetate. The combined organics were washed with 2×200 mL water, dried with brine and Na2SO4, and evaporated under reduced pressure. The residue was taken up in a minimum of diethyl ether and crystallized by adding sufficient hexane to precipatate the product. The solid was collected to give 7.74 g of 2,4-bis(trifluoromethyl) phenyl acetic acid as white crystals, 68.5%. NMR 1H (CDCl3) δ 7.93 (s, 1H), 7.80 (d, J=7.9 Hz,1H), 7.55 (d, J=7.9 Hz, 1H), 3.94 (s, 2H).
Workup
- extractionextracted with 2×300 mL ethyl acetate
- washThe combined organics were washed with 2×200 mL water
- dry with materialdried with brine and Na2SO4
- customevaporated under reduced pressure
- customcrystallized
- additionby adding sufficient hexane
- customThe solid was collected
Sources & evidence
- ORD record
- ord-6d72a2c9c9c844b7b0c5df8ca422b9cd
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05633251
Reaction notes
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