Sodium Hydroxide → 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid

Participants

Reaction Conditions

Reaction Steps

2.8 mL of NaOH 30% solution in water was diluted with 30 mL of water. The solution was heated to 55° C. and 3.0 g of adamantaneglyoxylic acid was dissolved therein. Then 3.3 g of potassium permanganate was added gradually during 2 h and stirring of obtained the obtained mixture was continued for 9 h at 55–60° C. The mixture was allowed to stay at room temperature for overnight. Then manganese dioxide precipitate was filtered out and the filtrate work-up procedure consisting of acidification, extraction with organic solvent and concentration of the combined organic phases resulted in 2.5 g of the target 3-hydroxyadamantaneglyoxylic acid (1) with purity 68.9% according to GC analysis of the corresponding methyl ester.

Provenance & Evidence