Sodium Hydroxide → 3,4-Difluorotoluene
Reaction equation
Cl[C:2]1([F:11])[C:7](F)([F:8])[CH2:6][C:5]([CH3:10])=[CH:4][CH2:3]1.ClC1(F)CC(C)=CCC1(F)F.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:8][C:7]1[CH:6]=[C:5]([CH3:10])[CH:4]=[CH:3][C:2]=1[F:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To a stirred mixture of 4-chloro-1-methyl-4,5,5-trifluorocyclohexene and 5-chloro-1-methyl-4,4,5-trifluorocyclohexene (1.20 kg) prepared in Example 1 was added 42 g of benzyltriethylammonium chloride, and then the reaction mixture was heated to 85° C. followed by slowly adding 2.15 kg of 50% aqueous sodium hydroxide solution over 4.5 hours. The reaction mixture was stirred for an additional 1.5 hours at 90° C. and then the resultant was purified by steam distillation followed by separating the aqueous layer. The organic layer was dried with 32 g of calcium chloride, and then 0.64 kg of the desired product was collected by fractional distillation at temperature range of 112° C. as a colorless liquid.
Workup
- distillationthe resultant was purified by steam distillation
- customby separating the aqueous layer
- dry with materialThe organic layer was dried with 32 g of calcium chloride
- distillation0.64 kg of the desired product was collected by fractional distillation at temperature range of 112° C. as a colorless liquid
Sources & evidence
- ORD record
- ord-bbdd0207161441e1b95cce84a0b655fa
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06008407
Reaction notes
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