Water → HCID 54444634, compound

HRID 1905825Notes

Reaction equation

HRID 1905825 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH:12]=O)=[CH:8][CH:7]=1)[CH2:3][CH3:4].N1C=CC=CC=1.Cl.[CH2:23]([O:25][NH2:26])[CH3:24].O>O1CCOCC1>[CH2:23]([O:25][N:26]=[CH:12][CH2:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH:2]([CH3:1])[CH2:3][CH3:4])=[CH:15][CH:14]=1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 13785598HCID 13785598, compound

Product 1

HCID 54444634HCID 54444634, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-(1-methylpropoxy)phenoxyacetaldehyde (0.68 g, 3.3 mmol) and pyridine (0.50 g, 6.3 mmol) in 5 ml of p-dioxane is added a solution of ethoxyamine hydrochloride (0.60 g, 6.2 mmol) in a minimum amount of water. The reaction mixture is stirred at RT for 6 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 removed in vacuo and the product is purified by column chromatography to give 4-(1-methylpropoxy)phenoxyacetaldehyde O-ethyloxime as a mixture of syn and anti stereo isomers. MS m/e 251 (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 removed in vacuo
  6. customthe product is purified by column chromatography

Sources & evidence

ORD record
ord-6faf71a7c3c14b3ebcde2327f7c2d7d6
Source dataset
uspto-grants-1987_03
Patent number
US04647698

Reaction notes

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