Reaction #41094

Reaction equation

5-Hydroxy-2-admantanone

hydroxylamine hydrochloride

→

5-hydroxy-adamantan-2-one oxime

Yield 73.4%

Solvents

EtOH

NaOH

Conditions

Workup

1. 1
   OtherThe EtOH was evaporated
2. 2
   workup.ADDITIONwater and dichloromethane were added
3. 3
   Filtrationfiltered
4. 4
   OtherThe solid was collected
5. 5
   OtherThe resulting mixture was separated
6. 6
   ExtractionThe aqueous layer was further extracted twice with dichloromethane
7. 7
   ConcentrationThe combined organic phases were concentrated under high vacuum
8. 8
   FiltrationThe resulting residue was combined with the solid from the filtration
9. 9
   OtherCrystallization from EtOAc

Procedure

5-Hydroxy-2-admantanone (15 g, 90.2 mmol, CAS #: 20098-14-0, purchased from TCI) was dissolved in EtOH (100 mL) and added to a solution of hydroxylamine hydrochloride (10 g, 143.9 mmol) in 1N NaOH (80 mL). The mixture was heated at 100° C. for 2 hours. The EtOH was evaporated, and water and dichloromethane were added. The resulting mixture was stirred for 10 min and then filtered. The solid was collected. The resulting mixture was separated. The aqueous layer was further extracted twice with dichloromethane. The combined organic phases were concentrated under high vacuum. The resulting residue was combined with the solid from the filtration. Crystallization from EtOAc gave 5-hydroxy-adamantan-2-one oxime (12 g, 73%). Mass spectrum: m/z: 182 (M+1).

Source