828-52-4

18720-35-9

828-52-4

General procedure for the synthesis of 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid from 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid: sodium borohydride (5.8 g, 0.15 mol) was added batchwise to an aqueous solution of 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (6.5 g, 0.03 mol) ( 120 mL) in water. The reaction mixture was stirred at room temperature overnight. Subsequently, the reaction mixture was cooled with ice water and the pH was adjusted to 2-3 with dilute aqueous hydrochloric acid (1.0 M). The solid was collected by filtration and the filter cake was washed with cold water (20 mL) and finally dried under reduced pressure to afford the target product 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid (5.66 g, yield: 100%) as a white solid.