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

Participants

Reaction Conditions

Reaction Steps

3.0 mL of NaOH 30% solutions in water was diluted with 120 mL of water. The solution was heated to 50° C. and 0.36 g of tetrabutylammonium bromide was added to the solution. Now 10 g of 1-acetyladamantane was added while stirring, followed by addition of 24.8 g of potassium permanganate during 4 h at 50–52° C. Stirring was continued for additional 4 h. The mixture was allowed to stay at room temperature for overnight and then manganese dioxide precipitate was filtered out. The filtrate work-up included acidification of filtrate, extraction and partial concentration of the combined organic phase. To the concentrated solution 10 mL of organic solvent was added and the mixture was kept at room temperature overnight. The formed crystals were filtered out, washed with solvent and dried to yield 4.7 g of the target 3-hydroxyadamantaneglyoxylic acid (1) with purity 96.4% according to GC analysis of the corresponding methyl ester.

Provenance & Evidence