Water → (1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acid
Reaction equation
[CH3:1][C:2]1([CH3:13])[CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:3]1[C:11]#N.[OH-:14].[K+].[OH2:16]>C(O)CO.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:13])[C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[C:11]([OH:16])=[O:14]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 165 °C
Procedure
A mixture of 2,2-dimethyl-3-phenyl-cyclopropanecarbonitrile (cis/trans mixture, 3.2 g, 18.7 mmol) and freshly ground KOH (3.143 g, 56.1 mmol) in ethylene glycol was heated at 165° C. for 28 hours. The reaction mixture was then cooled and poured into a mixture of water and brine (300 mL). The resulting mixture was extracted 3 times with ethyl ether, the combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give 3.36 g (95% yield) of trans-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid.
Workup
- temperatureThe reaction mixture was then cooled
- extractionThe resulting mixture was extracted 3 times with ethyl ether
- dry with materialthe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-26bc0c78278f40cc8951ed3d0ab7b1a9
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723391B2
Reaction notes
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