P-Cresol → alpha,alpha,beta,beta-Tetrafluoro-p-methylphenetole
Reaction equation
[F:1][C:2]([F:6])=[C:3]([F:5])[F:4].[CH:7]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]([CH3:14])[CH:8]=1.[OH-].[K+]>CN(C)C=O>[F:1][C:2]([F:6])([O:13][C:12]1[CH:7]=[CH:8][C:9]([CH3:14])=[CH:10][CH:11]=1)[CH:3]([F:5])[F:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 68 °C
Procedure
For one hour, tetrafluoroethylene and nitrogen are bubbled into a magnetically stirred mixture of 10.8 g (0.100 mol) of p-cresol, 1.67 g (1.67 g (1.43 g real, 0.0255 mol) of potassium hydroxide pellets, and 70 ml of dried dimethylformamide (DMF) maintained at 68° C. After dilution with 250 ml of water, the reaction mixture is extracted with 100 ml of ether. The ether solution is washed with 200 ml of 5% sodium hydroxide and twice with 400 ml of water. The ether solution is dried, filtered, and then rotary evaporated to give 18.14 g (87%) of p-(1,1,2,2-tetrafluoroethoxy)toluene.
Workup
- extractionAfter dilution with 250 ml of water, the reaction mixture is extracted with 100 ml of ether
- washThe ether solution is washed with 200 ml of 5% sodium hydroxide and twice with 400 ml of water
- dry with materialThe ether solution is dried
- filtrationfiltered
- customrotary evaporated
Sources & evidence
- ORD record
- ord-d2ed672761cb450ea8474733d360c254
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04199595
Reaction notes
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