Sodium Hydroxide → (1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime

HRID 1721501Notes

Reaction equation

HRID 1721501 reaction equation
[OH-:1].[Na+].[C@:3]12([CH3:13])[C:10]([CH3:12])([CH3:11])[CH:7]([CH2:8][CH2:9]1)[CH2:6][C:4]2=O.Cl.[NH2:15]O>C(O)C.O>[C@:3]12([CH3:13])[C:10]([CH3:12])([CH3:11])[CH:7]([CH2:8][CH2:9]1)[CH2:6][C:4]2=[N:15][OH:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 9543187Npc54264

Product 1

HCID 76039(1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Sodium hydroxide (15.03 g; 375.50 mmol) is added carefully to a solution, which is boiling under reflux, of (1R)(+)camphor (10.01 g; 65.86 mmol) and hydroxylamine hydrochloride (10.04 g; 144.46 mmol) in 150 ml of ethanol and 20 ml of water. After 7 hours, the reaction solution is cooled down, diluted with water and filtered. The filtrate is brought to a pH of 5-6 using acetic acid. After renewed filtration, the oxime 19 is obtained (3.81 g, 35% of theory) (m.p. 188°-20° C.).

Workup

  1. temperaturethe reaction solution is cooled down
  2. filtrationfiltered
  3. filtrationfiltration

Sources & evidence

ORD record
ord-f81fe3ffaf2a48548fa4631071726f13
Source dataset
uspto-grants-1996_04
Patent number
US05510504

Reaction notes

Loading…