Hydrochloric Acid → 4,4,4-Trifluoro-1-(4-methylphenyl)butane-1,3-dione
Reaction equation
C[O-].[Na+].[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:13])=[O:12])=[CH:7][CH:6]=1.C[O:15][C:16](=O)[C:17]([F:20])([F:19])[F:18].Cl>C1(C)C=CC=CC=1>[F:18][C:17]([F:20])([F:19])[C:16](=[O:15])[CH2:13][C:11]([C:8]1[CH:9]=[CH:10][C:5]([CH3:4])=[CH:6][CH:7]=1)=[O:12]Participants
Conditions
- Temperature
- 22.5 °C
Procedure
Sodium methoxide (25.6 g) and toluene (105 ml) were taken in a flask. A solution of 4-methylacetophenone (50 g) in toluene (52 ml) was added at 20-25° C. in 30 minutes. The resultant reaction mixture was stirred further at 20-25° C. for 30 minutes. A solution of methyltrifluoroacetate (56.8 g) in toluene (52 ml) was added slowly at 20-25° C. for about 1 hour and the reaction mixture was heated to about 110° C. for 24 hours. The reaction mixture was cooled to 30° C. and poured into a flask containing aqueous hydrochloric acid (210 ml, 3N). The layers were separated and the aqueous layer was extracted with toluene (2×50 ml). The organic layers were combined and washed with water (2×50 ml). The solvent was removed completely under vacuum to afford the title compound (Yield: 79 g).
Workup
- customThe resultant reaction mixture
- temperaturethe reaction mixture was heated to about 110° C. for 24 hours
- temperatureThe reaction mixture was cooled to 30° C.
- additionpoured into a flask
- customThe layers were separated
- extractionthe aqueous layer was extracted with toluene (2×50 ml)
- washwashed with water (2×50 ml)
- customThe solvent was removed completely under vacuum
Sources & evidence
- ORD record
- ord-9a3ae52f2a8745428aa0dcfb986a9697
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919633B2
Reaction notes
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