Thionyl Chloride → 2,2-Dimethyl-3-(2-trifluoromethyl-2-phenyl-vinyl)-cyclopropanecarboxylic acid chloride
Reaction equation
[CH3:1][C:2]1([CH3:20])[CH:4]([CH:5]=[C:6]([C:13]([F:16])([F:15])[F:14])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]1[C:17](O)=[O:18].S(Cl)([Cl:23])=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:20])[CH:4]([CH:5]=[C:6]([C:13]([F:16])([F:15])[F:14])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]1[C:17]([Cl:23])=[O:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
7.1 g (0.025 mol) of 2,2-dimethyl-3-(2-trifluoromethyl-2-phenyl-vinyl)-cyclopropanecarboxylic acid were dissolved in 100 ml of carbon tetrachloride, and 9 g of thionyl chloride were slowly added dropwise at 25° C., while stirring. The mixture was then heated to the reflux temperature for 4 hours. After this reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum. The oil which remained was freed from last residues of solvent by brief incipient distillation at a bath temperature of 40° C./2 mm Hg. 7 g (92.7% of theory) of 2,2-dimethyl-3-(2-trifluoromethyl-2-phenyl-vinyl)-cyclopropanecarboxylic acid chloride were obtained. The structure was confirmed by the 1H-NMR spectrum.
Workup
- temperatureThe mixture was then heated to the reflux temperature for 4 hours
- distillationAfter this reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum
- distillationThe oil which remained was freed from last residues of solvent by brief incipient distillation at a bath temperature of 40° C./2 mm Hg
Sources & evidence
- ORD record
- ord-ecc3537ae98247f0b058b311d7f2425d
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04485252
Reaction notes
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