N-Methylmorpholine N-oxide monohydrate → Methyl alpha-(2-formylphenyl)-beta-methoxyacrylate

HRID 1656702

Reaction equation

HRID 1656702 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11].O.C[N+]1([O-])CC[O:22]CC1>C(Cl)(Cl)(Cl)Cl>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[O:22]

Participants

4

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 53811047Methyl alpha-(2-formylphenyl)-beta-methoxyacrylateYield 67.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

35.5 g (0.125 mol) of methyl alpha-(2-bromomethylphenyl)-β-methoxyacrylate are dissolved in 500 ml of CCl4. 43.4 g (0.321 mol) of methylmorpholine N-oxide monohydrate are added, and the mixture is refluxed for 20 hours. The solid is filtered of f and the CCl4 phase is washed with water, with 2 N hydrochloric acid and again with water, dried and concentrated. 18.5 g (67%) of product are obtained as a reddish brown oil.

Workup

  1. temperaturethe mixture is refluxed for 20 hours
  2. filtrationThe solid is filtered of f
  3. washthe CCl4 phase is washed with water, with 2 N hydrochloric acid and again with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-146f12103baa42ee9b84cc65d41ab655
Source dataset
uspto-grants-1993_10
Patent number
US05254717

Linked notes

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