Potassium Carbonate → 1-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylic Acid
Reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:9][C:10]([C:12]1([C:23]#[N:24])[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]1([CH3:22])[CH3:21])=[O:11])C>O.CO>[C:23]([C:12]1([C:10]([OH:11])=[O:9])[CH:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:13]1([CH3:22])[CH3:21])#[N:24]Participants
Conditions
- Temperature
- 85 °C
Procedure
A solution of potassium carbonate (40 g) in water (125 mL) was added to a solution of 1-cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid ethyl ester (64.26 g, 264 mmol) in MeOH (500 mL). The reaction mixture was heated at reflux for 1 hour and then stirred overnight at 85° C. The volatiles where evaporated under reduced pressure, and the residue was diluted with water and washed twice with EtOAc. The phases were separated and the aqueous phase was acidified by addition of HCl (concentrated). Ethyl ether was added and the mixture was carefully extracted. The organic layer was separated, dried over Na2SO4, filtered and evaporated under reduced pressure to give 27.2 g (49% yield) of 1-cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid as an off-white solid.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux for 1 hour
- customThe volatiles where evaporated under reduced pressure
- additionthe residue was diluted with water
- washwashed twice with EtOAc
- customThe phases were separated
- additionthe aqueous phase was acidified by addition of HCl (concentrated)
- additionEthyl ether was added
- extractionthe mixture was carefully extracted
- customThe organic layer was separated
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-f003c08da0fe4b25897e2572e3b0361f
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723391B2
Reaction notes
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