Hydrochloric Acid → 4-Methoxybicyclo(2.2.2)octane-1-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]([O:13]C)=[O:12])([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.Cl>[OH-].[Na+]>[CH3:1][O:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]([OH:13])=[O:12])([CH2:5][CH2:4]1)[CH2:7][CH2:8]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 4-methoxybicyclo[2.2.2]octane-1-carboxylate (6.5 g, 33 mmol) was refluxed in aqueous sodium hydroxide solution (5%, 150 mL) for 2 h. After cooling down, the reaction solution was acidified with hydrochloric acid solution (6 N, 50 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were dried over magnesium sulfate and concentrated to afford the title compound (5.9 g, 32 mmol, yield 97%) which was used in the next step without further purification. MS (ESI) m/z=183.2 [M+H]−.