Water → HCID 53825902, compound

HRID 1905826Notes

Reaction equation

HRID 1905826 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][C:12](=O)[CH3:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4].N1C=CC=CC=1.Cl.[CH2:24]([O:26][NH2:27])[CH3:25].O>O1CCOCC1>[CH2:24]([O:26][N:27]=[C:12]([CH2:11][O:10][C:9]1[CH:15]=[CH:16][C:6]([O:5][CH:2]([CH3:1])[CH2:3][CH3:4])=[CH:7][CH:8]=1)[CH3:13])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 20215483HCID 20215483, compound

Product 1

HCID 53825902HCID 53825902, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-(1-methylpropoxy)phenoxyacetone (0.70 g, 3.1 mmol) and pyridine (0.50 g, 6.3 mmol) in 10 ml of p-dioxane is added a solution of ethoxyamine hydrochloride (0.70 g, 7.2 mmol) in a minimum amount of water. The reaction mixture is stirred at RT for 16 hours, after which the dioxane is removed in vacuo. The residue is taken up in ether and the organic layer is washed with water. The aqueous phase is extracted with ether, and the combined organic phases are dried, the solvent is evaporated off and the product is purified by column chromatography to give 4-(1-methylpropoxy)phenoxyacetone O-ethyloxime, MS m/e 265 (M+).

Workup

  1. customafter which the dioxane is removed in vacuo
  2. washthe organic layer is washed with water
  3. extractionThe aqueous phase is extracted with ether
  4. customthe combined organic phases are dried
  5. customthe solvent is evaporated off
  6. customthe product is purified by column chromatography

Sources & evidence

ORD record
ord-7e0d03f52b9b413585ce48c12e811417
Source dataset
uspto-grants-1987_03
Patent number
US04647698

Reaction notes

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