Methanol → Methyl 2,2,3-trifluoro-3-[1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propoxy]propanoate
Reaction equation
[C:1]([O:5][C:6]([C:9]([C:12]([O:15][CH:16]([C:18]([CH2:21][OH:22])([F:20])[F:19])[F:17])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7])([F:4])([F:3])[F:2].S(=O)(=O)(O)O.[O-][Mn](=O)(=O)=O.[K+].S(=O)(O)[O-].[Na+].[CH3:39][OH:40]>O>[C:1]([O:5][C:6]([C:9]([C:12]([O:15][CH:16]([C:18]([C:21]([O:40][CH3:39])=[O:22])([F:19])[F:20])[F:17])([F:13])[F:14])([F:11])[F:10])([F:8])[F:7])([F:4])([F:3])[F:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A 2 liter glass flask equipped with a thermometer, reflux condenser, dropping funnel and stirrer was used. 159 g of CF3O(CF2)3OCHFCF2CH2OH, 520 g water, and 100 g sulfuric acid were added to the flask. 190 g KMnO4 were added manually to the liquid over a period of 2 hours while stirring. The reaction temperature increased to 95° C. over time. After a post reaction time of two hours, an aqueous solution of sodium bisulfite was added until a clear solution was formed. 100 g of methanol and in total 400 g of 50% aqueous sulphuric acid were added. Flash distillation of the reaction mixture resulted in a two phase distillate. Fractionation of the lower phase (120 g) gave 85.5 g of CF3O(CF2)3OCHFCF2COOCH3 (bp 34-35° C./6 mbar; yield 50%).
Workup
- customA 2 liter glass flask equipped with a thermometer
- temperaturereflux condenser
- customAfter a post reaction time of two hours
- customwas formed
- distillationFlash distillation of the reaction mixture
- customresulted in a two phase distillate
Sources & evidence
- ORD record
- ord-739df4646dde47e780271ff7c13d32e6
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754795B2
Reaction notes
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