Hydroxylamine HCl → 6-Butoxy-2,2-dimethylchroman-4-one oxime

HRID 618822Notes

Reaction equation

HRID 618822 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([CH3:17])([CH3:16])[CH2:10][C:9]2=O)[CH2:2][CH2:3][CH3:4].[Cl-].[OH:20][NH3+:21].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([CH3:17])([CH3:16])[CH2:10][C:9]2=[N:21][OH:20])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 110540056-Butoxy-2,2-dimethylchroman-4-one

Product 1

HCID 867545196-Butoxy-2,2-dimethylchroman-4-one oximeYield 100.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 52.0 g (0.21 mol) of 6-butoxy-2,2-dimethylchroman-4-one in 420 ml of ethanol were added dropwise in 30 min to a solution of 43.7 g (0.628 mol) of hydroxylammonium chloride and 51.5 g (0.628 mol) of sodium acetate in 420 ml of water and the mixture was kept at 60° C. for 3 h. The oily product phase was separated off and the aqueous phase was extracted with methylene chloride. After drying the organic phases over magnesium sulfate and concentrating in vacuo, 55.5 g of 6-butoxy-2,2-dimethylchroman-4-one oxime were obtained, which it was possible to crystallize by stirring with PE.

Workup

  1. customThe oily product phase was separated off
  2. extractionthe aqueous phase was extracted with methylene chloride
  3. dry with materialAfter drying the organic phases over magnesium sulfate
  4. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-f6d3c350120946078188c82c9593e6ee
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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