Water → 3-Hydroxyiminocamphor

HRID 1885758Notes

Reaction equation

HRID 1885758 reaction equation
[Na].[N:2](OCCC(C)C)=[O:3].O.[CH3:11][C@:12]12[C:20](=[O:21])[CH2:19][C@H:15]([C:16]1([CH3:18])[CH3:17])[CH2:14][CH2:13]2>C(OCC)C>[OH:3][N:2]=[C:19]1[CH:15]2[C:16]([CH3:17])([CH3:18])[C:12]([CH3:11])([CH2:13][CH2:14]2)[C:20]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8053Isoamyl NitriteHCID 159055D-CamphorHCID 5360545Sodium

Product 1

HCID 68447213-Hydroxyiminocamphor

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In 600 ml of dried diethyl ether was dissolved 130 g (0.854 mol) of commercially available D-camphor, and 20.4 g of metallic sodium was added thereto. The solution was kept at 0° C. with stirring, and 123 ml (0.916 mol) of isoamyl nitrite was added thereto to conduct a reaction for 14 hours. After completion of the reaction, 200 ml of water was added to the reaction mixture, and the aqueous layer was separated. To the aqueous layer was added 400 ml of 10% hydrochloric acid, and the solid thus formed was extracted with diethyl ether. The ether layer was dried and concentrated to obtain 51 g of 3-hydroxyiminocamphor.

Workup

  1. additionwas added
  2. customwas kept at 0° C.
  3. customa reaction for 14 hours
  4. additionwas added to the reaction mixture
  5. customthe aqueous layer was separated
  6. additionTo the aqueous layer was added 400 ml of 10% hydrochloric acid
  7. customthe solid thus formed
  8. extractionwas extracted with diethyl ether
  9. dry with materialThe ether layer was dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bbc06c0a733b42528dbf80318ceaf1c1
Source dataset
uspto-grants-1992_09
Patent number
US05146003

Reaction notes

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