Hydrochloric Acid → 4,4,4-Trifluoro-1-(4-methylphenyl)butane-1,3-dione
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[O:9])=[CH:4][CH:3]=1.C([O:14][C:15](=O)[C:16]([F:19])([F:18])[F:17])(C)C.C[O-].[Na+].Cl>O.C1(C)C=CC=CC=1>[F:17][C:16]([F:19])([F:18])[C:15](=[O:14])[CH2:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:9]Participants
7
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 4-methylacetophenone (0.85 g), isopropyltrifluoroacetate (1.0 g) and toluene (2 ml) was added to a mixture of sodium methoxide (0.4 g) and toluene (2 ml) at 35-40° C. The reaction mixture was stirred at 75° C. for 4 hours. The reaction mixture was cooled to 25-30° C. Water (2 ml) and aqueous HCl (3 ml, 20%) were added and the reaction mixture was stirred at 25-30° C. for 30 minutes. The layers were separated. Aqueous layer was extracted with toluene (2×2 ml). The organic layers were combined and the solvent was removed by distillation at 55° C. under vacuum to obtain the title compound (Yield: 1.0 g).
Workup
- temperatureThe reaction mixture was cooled to 25-30° C
- stirringthe reaction mixture was stirred at 25-30° C. for 30 minutes
- customThe layers were separated
- extractionAqueous layer was extracted with toluene (2×2 ml)
- customthe solvent was removed by distillation at 55° C. under vacuum
Sources & evidence
- ORD record
- ord-977169946fe141e398bda92f3d84eac3
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919633B2
Reaction notes
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