Hydrochloric Acid → 4-Hydroxybicyclo[2.2.2]octane-1-carboxylic acid

Reaktionsgleichung

Br[C:2]12[CH2:9][CH2:8][C:5]([C:10]([O:12]C)=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Cl.[OH-:15].[Na+]>>[OH:15][C:2]12[CH2:9][CH2:8][C:5]([C:10]([OH:12])=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Komponenten

Edukt 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 57467434Methyl 4-bromobicyclo(2.2.2)octane-1-carboxylate

Produkt 1

HCID 125601364-Hydroxybicyclo[2.2.2]octane-1-carboxylic acidAusbeute 89 %

Versuchsvorschrift

Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate (17.0 g, 69.0 mmol) was refluxed in 1.5 L of 1% aqueous sodium hydroxide solution for 24 h. After cooling down, the reaction solution was acidified with hydrochloric acid (6N, 100 mL) and extracted with diethyl ether (6×500 mL). The combined organic layers were dried over magnesium sulfate and concentrated to afford the titled compound (10.4 g, 61.1 mmol, yield: 89%), which was used in the next step without further purification; MS (ESI) m/z=169.2 [M+H]−.