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1-(2,6-Dimethoxyphenyl)ethanone → Methyl 4-(2,6-dimethoxyphenyl)-4-oxido-2-oxo-3-butenoate sodium salt

HRID 259896
Notes
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Reaction equation

HRID 259896 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[O:12][CH3:13])=[O:3].[C:14]([O:19][CH2:20]C)(=[O:18])[C:15]([O-])=[O:16].C[O-].[Na+:24].[Na]>CO.CCOCC>[Na+:24].[CH3:13][O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH3:11])[C:4]=1[C:2]([O-:3])=[CH:1][C:15](=[O:16])[C:14]([O:19][CH3:20])=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 162671-(2,6-Dimethoxyphenyl)ethanoneHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 21943339Ethanedioic acid, monoethyl ester

Product 1

HCID 70245405Methyl 4-(2,6-dimethoxyphenyl)-4-oxido-2-oxo-3-butenoate sodium salt

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
2×
HCID 3283Diethyl EtherSolvent

Procedure

A solution of 100 g of 2,6-dimethoxyacetophenone and 7.5 ml of ethyl oxalate in 520 ml of anhydrous MeOH is added slowly to a solution of sodium methylate prepared from 12.7 g of sodium and 285 ml of anhydrous MeOH. The reaction mixture is heated to reflux for 7 hours and left overnight at RT. It is poured into 2 liters of iso ether and left stirring for minutes. The expected product is obtained by filtration, washing with iso ether and drying under vacuum, m=120 g, m.p.=178° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 7 hours
  3. waitleft

Sources & evidence

ORD record
ord-f2232b314c4f4f0c8f5f35546d456b8e
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05523455

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes