Diethyl Oxalate → Ethyl 2,4-dioxo-4-(2,4,6-trimethylphenyl)butanoate

HRID 1266151

Reaction equation

HRID 1266151 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11].[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].[H-].[Na+]>C1(C)C=CC=CC=1>[O:19]=[C:13]([CH2:11][C:10](=[O:12])[C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 15461Ethanone, 1-(2,4,6-trimethylphenyl)-HCID 24758Sodium hydride

Product 1

HCID 14945000Ethyl 2,4-dioxo-4-(2,4,6-trimethylphenyl)butanoateYield 66.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2′,4′,6′-trimethylacetophenone (15 g, 92.6 mmol) and diethyl oxalate (20 g, 139 mmol) in 500 mL of anhydrous toluene was cautiously added 7.4 g of NaH (60% dispersion in mineral oil). The reaction mixture was slowly heated to reflux under N2. It was refluxed for about 20 minutes, then cooled, poured into ice-cold aqueous HCl solution, and extracted with ether. The extracts were washed with brine, dried over Na2SO4, filtered through a short silica gel pad and concentrated to give 16.2 g of a red oil which was used in the next reaction without further purification.

Workup

  1. temperatureThe reaction mixture was slowly heated
  2. temperatureto reflux under N2
  3. temperatureIt was refluxed for about 20 minutes
  4. temperaturecooled
  5. additionpoured into ice-cold aqueous HCl solution
  6. extractionextracted with ether
  7. washThe extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered through a short silica gel pad
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7432959959ea4e969bb39a1eafd17f2a
Source dataset
uspto-grants-2003_04
Patent number
US06548509B2

Linked notes

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