N-Methylmorpholine N-oxide monohydrate → methyl 2-formylphenylglyoxylate O-methyloxime

HRID 1656703Notes

Reaction equation

HRID 1656703 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]Br)[C:5]([O:7][CH3:8])=[O:6].O.C[N+]1([O-])CC[O:22]CC1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[O:22])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

Product 1

HCID 54338916methyl 2-formylphenylglyoxylate O-methyloximeYield 58.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

20 g (0.070 mol) of methyl 2-(bromomethyl)phenylglyoxylate O-methyloxime, 32 g (0.237 mol) of N-methylmorpholine N-oxide monohydrate and 300 ml of CCl4 are mixed and heated to reflux. After refluxing for 9 hours, the mixture is filtered, and the organic phase is washed with water and with 2 N hydrochloric acid, dried and concentrated. The residue is recrystallized from pentane. 9.0 g of product (58%) are obtained as colorless crystals.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter refluxing for 9 hours
  3. filtrationthe mixture is filtered
  4. washthe organic phase is washed with water and with 2 N hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is recrystallized from pentane

Sources & evidence

ORD record
ord-761e678284d84d968ff8bd9608f6af2a
Source dataset
uspto-grants-1993_10
Patent number
US05254717

Reaction notes

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