1-Butanol → 3,5-Dihydroxyadamantane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.14 mol of the obtained 3,5-dihydroxy-1-adamantanecarboxylic acid, 1.4 mol of n-butanol and 3.5 mmol of sulfuric acid was stirred at 100° C. for 8 hours. To the reaction mixture were added a saturated sodium chloride aqueous solution and a 5% sodium hydroxide aqueous solution (NaOH: 3.5 mmol), and the resultant mixture was subjected to separation. The organic layer was concentrated, and the concentrated residue was subjected to recrystallization from toluene to give n-butyl 3,5-dihydroxy-1-adamantanecarboxylate in yield of 86% at a conversion rate from 3,5-dihydroxy-1-adamantanecarboxylic acid of 99%.

Provenance & Evidence