p-Toluenesulfonic acid → 1-(2-Nitro-4-trifluoromethylphenyl)-butan-1,3-dione
Reaction equation
[N+:1]([C:4]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:5]=1[C:6]([CH:8]([C:16](=[O:18])[CH3:17])C(OC(C)(C)C)=O)=[O:7])([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[N+:1]([C:4]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:5]=1[C:6](=[O:7])[CH2:8][C:16](=[O:18])[CH3:17])([O-:3])=[O:2]Participants
3
Procedure
A mixture of crude t-butyl 2-(2-nitro-4-trifluoromethylbenzoyl)-3-oxobutanoate (9.1 g) and 4-toluenesulphonic acid (0.1 g) in dry, toluene (100 ml) was stirred and heated at reflux for 3 hours. The cooled mixture was extracted with aqueous sodium hydroxide solution (2M, 2×50 ml) and water (2×50 ml). The combined aqueous extracts were acidified to pH 1 and extracted with ether (3×100 ml). The combined organic layers were washed with water (50 ml), dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from petroleum spirit (bp 60°-80° C.) to give 1-(2-nitro-4-trifluoromethylphenyl)-butan-1,3-dione (4.6 g) as an off white solid mp 80°-81° C.
Workup
- customin dry
- temperatureheated
- temperatureat reflux for 3 hours
- extractionThe cooled mixture was extracted with aqueous sodium hydroxide solution (2M, 2×50 ml) and water (2×50 ml)
- extractionextracted with ether (3×100 ml)
- washThe combined organic layers were washed with water (50 ml)
- dry with materialdried (anhydrous sodium sulphate)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was recrystallized from petroleum spirit (bp 60°-80° C.)
Sources & evidence
- ORD record
- ord-57c1e79f80054d6d9743ff2dce3eaf08
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05656573
Reaction notes
Loading…