Triethylamine → 4-(Methoxymethoxy)-3-methylbenzaldehyde oxime

HRID 393270Notes

Reaction equation

HRID 393270 reaction equation
CCN(CC)CC.Cl.[NH2:9][OH:10].[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[CH3:23]>O1CCOCC1.CCOC(C)=O>[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[N:9][OH:10])=[CH:17][C:16]=1[CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 226488754-(Methoxymethoxy)-3-methylbenzaldehyde

Product 1

HCID 739911594-(Methoxymethoxy)-3-methylbenzaldehyde oximeYield 86.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

Et3N (1.68 mL, 12.0 mmol) and hydroxylamine hydrochloride (320 mg, 4.64 mmol) were added to a solution of 4-(methoxymethoxy)-3-methylbenzaldehyde (620 mg, 3.44 mmol) in 1,4-dioxane (12 mL). The reaction mixture was sonicated for 10 min and stirred at 25° C. for 3 d. The reaction mixture was diluted with EtOAc and successively washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 3:1) to provide the title compound (580 mg, 86% yield) as a clear gum.

Workup

  1. customThe reaction mixture was sonicated for 10 min
  2. washsuccessively washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (Hexane:EtOAc, 3:1)

Sources & evidence

ORD record
ord-215eb0fea9fe401f9c785fc120fafbe8
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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