반응 #2028872

반응 방정식

HCl

Dimethyl oxalate

sodium methoxide

methanol

4′-chloroacetophenone

→

yellow solid

수율 95.0%

Methyl-4-[4-(chloro)phenyl]-2,4-dioxobutanoate

수율 95.0%

용매

ethyl acetate

diethyl ether

diethyl ether

반응 조건

후처리

1. 1
   workup.ADDITIONadded to the reaction dropwise over 3 minutes
2. 2
   workup.ADDITIONwere added
3. 3
   기타The organic layer was collected
4. 4
   세척washed with brine (350 mL)
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo

실험 절차

Dimethyl oxalate (23.6 g, 200 mmol) was placed in a 500 mL three-necked round bottom flask, and dissolved in diethyl ether (200 mL). To the stirred solution was added 25% sodium methoxide in methanol (48 mL, 210 mmol) via an addition funnel over a 2 minute period. Next, 4′-chloroacetophenone (25.94 g, 200 mmol) was dissolved in diethyl ether (50 mL), and added to the reaction dropwise over 3 minutes. After stirring overnight (18 hours), 1N HCl (400 mL) and ethyl acetate (750 mL) were added. The organic layer was collected, washed with brine (350 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 45.7 g of a yellow solid. The solid was recrystallized from ethyl acetate and iso-octane to give 23 g (48%) of the dione: mp 108.5°-110.5° C.

출처