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

HRID 565808

Reaction equation

HRID 565808 reaction equation
CC([O-])(C)C.[K+:6].[CH3:7][C:8]([C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19])=[O:9].[C:20]([O:25][CH2:26][CH3:27])(=[O:24])[C:21]([O-])=[O:22]>C(O)C>[K+:6].[CH3:19][O:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:10]=1[C:8]([O-:9])=[CH:7][C:21](=[O:22])[C:20]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 162671-(2,6-Dimethoxyphenyl)ethanoneHCID 21943339Ethanedioic acid, monoethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 70244972Ethyl 4-(2,6-dimethoxyphenyl)-4-oxido-2-oxo-3-butenoate potassium salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 13.4 g of 95% potassium tert-butylate in 72 ml of ethanol is added over 6 minutes to a solution, stirred and heated to 50° C., of 18 g of 2,6-dimethoxyacetophenone in 54 ml of ethanol. The mixture is heated to reflux, 16.3 ml of ethyl oxalate are added over 9 minutes and refluxing is continued for 1 hour. 40 ml of ethanol are then distilled off and the mixture is allowed to cool with stirring for two and a half hours. The mixture is filtered, and the precipitate is washed with 40 ml of ethanol and dried under vacuum at 60° C. for 17 hours to obtain 31 g of expected product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperaturerefluxing
  4. distillation40 ml of ethanol are then distilled off
  5. temperatureto cool
  6. stirringwith stirring for two and a half hours
  7. filtrationThe mixture is filtered
  8. washthe precipitate is washed with 40 ml of ethanol
  9. customdried under vacuum at 60° C. for 17 hours

Sources & evidence

ORD record
ord-6da63e9d4b604faf86ddf6e0b5b24e35
Source dataset
uspto-grants-2001_01
Patent number
US06172239B2

Linked notes

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