Lithium hydroxide, monohydrate → 3-Cyclopropyl-3-methylbutanoic acid
Reaction equation
C([O:3][C:4](=[O:12])[CH2:5][C:6]([CH:9]1[CH2:11][CH2:10]1)([CH3:8])[CH3:7])C.O.[OH-].[Li+]>C1COCC1.O.CO.O>[CH:9]1([C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([OH:12])=[O:3])[CH2:11][CH2:10]1Participants
5
Procedure
A mixture of 3-cyclopropyl-3-methylbutyric acid ethyl ester (3.0 g, 17.6 mmol) and lithium hydroxide monohydrate (3.5 g, 105 mmol) in THF/H2O/MeOH (24 mL, 2:1:1 v/v) was stirred at rt overnight. The reaction mixture was diluted with water (100 mL), and washed with ethyl acetate (2×50 mL). The aqueous layer was acidified with 2M HCl and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (200 mL), dried over sodium sulfate and concentrated to give 3-cyclopropyl-3-methylbutyric acid.