[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]
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.
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