Reaktion #1248

Reaktionsgleichung

2', 4', 6'-trimethylacetophenone

diethyl oxalate

NaH

→

red oil

Ausbeute 66.7%

Ethyl 2,4-dioxo-4-(2,4,6-trimethylphenyl)butanoate

Ausbeute 66.7%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was slowly heated
2. 2
   Temperaturto reflux under N2
3. 3
   TemperaturIt was refluxed for about 20 minutes
4. 4
   Temperaturcooled
5. 5
   workup.ADDITIONpoured into ice-cold aqueous HCl solution
6. 6
   Extraktionextracted with ether
7. 7
   WaschenThe extracts were washed with brine
8. 8
   Trocknendried over Na2SO4
9. 9
   Filtrationfiltered through a short silica gel pad
10. 10
    Einengenconcentrated

Vorschrift

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.

Quelle