Catechol → 2-(2,2,2-Trifluoroethoxy)phenol
Reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].[F:15][C:16]([F:20])([F:19])[CH2:17]I.O>CS(C)=O>[F:15][C:16]([F:20])([F:19])[CH2:17][O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To a solution of catechol (5 g, 0.045 moles) in dimethylsulfoxide (25 ml) were added, potassium carbonate (12.55 g, 0.09 mole) and 2,2,2-trifluoroethyl iodide (4.77 g, 0.023 mole) under stirring. The reaction mixture was stirred vigorously at 120° C. for 6 hours. Water (150 ml) was added to the reaction mixture and the mixture was extracted in Toluene (250 ml). Organic layer was washed with 1 N Sodium hydroxide solution (150 ml), followed by brine wash. The extract was dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC)=96%
Workup
- extractionthe mixture was extracted in Toluene (250 ml)
- washOrganic layer was washed with 1 N Sodium hydroxide solution (150 ml)
- washwash
- dry with materialThe extract was dried over sodium sulphate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-9c021d17ce3549ae85fa3aeba0cc78bc
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471039B2
Reaction notes
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