Water → 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid

Participants

Reaction Steps

30 g of 1-acetyladamantane was added to solution of 6.8 g of NaOH in 500 mL of water. The temperature of the suspension was increased to 40–50° C. and 80 g of potassium permanganate was added during a period of 1.5 h. The obtained mixture was stirred at 50–55° C. for 6 h and thereafter at room temperature 27° C. for 17 h followed by separation of the formed manganese dioxide precipitate by means of filtration. After the filtrate work-up that included acidification of filtrate, extractions with organic solvent and concentration of the combined organic phases, 28 g of partly crystallized material was obtained. Recrystallization of the material gave 13.6 g of the target 3-hydroxyadamantaneglyoxylic acid (1) as white crystalline solid with the purity 92.1% according to GC analysis of the corresponding methyl ester.

Provenance & Evidence