Hydrochloric Acid → Adamantane-1,4-diol

Beteiligte Stoffe

Reaktionsschritte

A stirred solution of 1-hydroxy-4-adamantanone (10.53 g, 63.4 mmol) in MeOH (100 mL) was cooled in an ice bath and NaBH4 (5×1-g caplets, 5.0 g, 130 mmol) was added. The ice bath was allowed to melt and the mixture was stirred overnight. 5% aq HCl (25 mL) was added and the mixture was concentrated to leave a white solid. This material was suspended in EtOAc (350 mL) and 5% aq HCl (100 mL) and filtered. The organic layer of the filtrate was collected, washed with brine, dried over Na2SO4 and concentrated to afford 1,4-adamantanediol (4.47 g, 41%).

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