Water → HCID 721748, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available 2-adamantanone (×1) (1000 g, 6.66 mol, Sigma-Aldrich) was dissolved in TFA (3 L, Sigma-Aldrich). To this mechanically stirred mixture surrounded by a cooling bath with a temperature maintained at 20° C. was added sodium percarbonate (1254.8 g, 7.99 mol, Sigma-Aldrich) (or sodium peroxocarbonate) portion-wise over 1 h; the temperature of the reaction mixture increased to 60° C. during the addition. After 2 h additional stirring, deionized water (4 L) was added followed by four extractions with DCM (2 L for each extraction). The organic portions were combined, dried (MgSO4), filtered, and evaporated under reduced pressure to provide 1180 g of (1R,3r,6s,8S)-4-oxatricyclo[4.3.1.13,8]undecan-5-one (×2) as a white crystalline solid (yield 97%).

Provenance & Evidence