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2-hydroxybenzaldehyde O-methyloxime → Methyl 2-(2-methoxyiminomethylphenoxymethyl)phenylglyoxylate O-methyloxime

HRID 1591138
Notes
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Reaction equation

HRID 1591138 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].C[O-].[Na+].[CH3:15][O:16][N:17]=[C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29]Br)[C:19]([O:21][CH3:22])=[O:20]>CO.CN(C)C=O.C(OCC)(=O)C>[CH3:15][O:16][N:17]=[C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:4]=[N:3][O:2][CH3:1])[C:19]([O:21][CH3:22])=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 5232402-hydroxybenzaldehyde O-methyloximeHCID 10942334Sodium MethoxideHCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

Product 1

HCID 53961752Methyl 2-(2-methoxyiminomethylphenoxymethyl)phenylglyoxylate O-methyloxime

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

3.0 g (20 mmol) of 2-hydroxybenzaldehyde O-methyloxime are dissolved in 20 ml of methanol, and 3.6 g (20 mmol) of sodium methanolate (30% strength in methanol) are added. The mixture is refluxed for four hours and then concentrated. The residue is taken up in 100 ml of dimethylformamide, and 6.5 g (23 mmol) of methyl 2-bromomethylphenylglyoxylate O-methyloxime in 50 ml of dimethylformamide are added. The mixture is stirred at 100° C. for 5 hours, the solvent is stripped off, and the residue is taken up in ethyl acetate. The organic phase is washed with water, dried and concentrated. The residue is triturated with pentane to induce crystallization. 4.8 g (67% of theory) of the title compound are obtained in the form of colorless crystals (melting point 73°-76° C., compound no. 2).

Workup

  1. temperatureThe mixture is refluxed for four hours
  2. concentrationconcentrated
  3. washThe organic phase is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is triturated with pentane
  7. customcrystallization

Sources & evidence

ORD record
ord-b2d5b3c075ea450e89e5767d59c6b665
Source dataset
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05206266

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes