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

Participants

Reaction Steps

1.7 mL of NaOH 30% solution in water was diluted with 500 mL of water and 60 g of 1-acetyladamantane was added to that solution. Temperature of the suspension was increased to 35–40° C. and 144 g of potassium permanganate was added to the suspension during 0.5 h. The mixture was stirred at 35–40° C. for 25 h followed by manganese dioxide precipitate filtration. The filtrate work-up procedure consisting of acidification, extractions with organic solvent and concentration of the combined organic phases which resulted in 25.2 g of the target 3-hydroxyadamantaneglyoxylic acid (1) with purity 85.7% according to GC analysis of the corresponding methyl ester.

Provenance & Evidence