Triethylamine → 3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oxime

HRID 585638Notes

Reaction equation

HRID 585638 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=O)[CH:16]=1.Cl.[NH2:23][OH:24].C(N(CC)CC)C>C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[N:23][OH:24])[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 121351713-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one

Product 1

HCID 738836023-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oximeYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one (200 mg), hydroxylamine hydrochloride (72 mg) and triethylamine (0.14 ml) were heated under reflux in ethanol (10 ml). After 3 hr, the cooled reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated in vacuo to furnish the title compound as an oil (206 mg, 99%). m/z (ES+) 308 (M+H)+.

Workup

  1. customthe cooled reaction mixture
  2. customwas partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d3130c5b0f8e4409b64bb6a8ac73ab00
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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