Hydroxyamine hydrochloride → HCID 23457011, compound

HRID 917934Notes

Reaction equation

HRID 917934 reaction equation
[CH3:1][C:2](/[CH:4]=[CH:5]/[CH:6]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:7]1=[CH2:8])=[O:3].Cl.NO.C([O-])(=[O:20])C.[Na+]>C(O)C.O>[CH2:8]=[C:7]1[CH2:9][CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[CH:6]1[C:5](=[O:20])[CH2:4][C:2](=[O:3])[CH3:1]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 536374179-76-5

Product 1

HCID 23457011HCID 23457011, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 30 g of γ-ionone in 75 ml of ethanol was added to a solution of hydroxylamine hydrochloride (12 g) and sodium acetate (21.6 g) in 30 ml of water. The addition was completed within 5 minutes. The reaction was slightly exothermic, the reaction mixture was stirred for 30 minutes, then it was concentrated under reduced pressure. Thereafter 30 ml of water and 30 ml of ether were added to the said mixture, and it was extracted with petroleum-ether. After drying and concentration, the combined organic extracts yielded a thick oil (31.2 g). An aliquot was distilled in a small distillation tube at a temperature of 180° and a pressure of 0.001 Torr. There was thus obtained a pure product which, as shown by vapour phase chromatography, constituted a mixture of the γ-ionone oxime in the form of the two syn- and anti-isomers in a ratio of 20:80.

Workup

  1. additionThe addition
  2. concentrationit was concentrated under reduced pressure
  3. additionThereafter 30 ml of water and 30 ml of ether were added to the said mixture, and it
  4. extractionwas extracted with petroleum-ether
  5. customAfter drying
  6. concentrationconcentration

Sources & evidence

ORD record
ord-b9090f7e520f4833b361c75de1b214a9
Source dataset
uspto-grants-1976_07
Patent number
US03968161

Reaction notes

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