反応 #2028872

反応方程式

HCl

Dimethyl oxalate

sodium methoxide

methanol

4′-chloroacetophenone

→

yellow solid

収率 95.0%

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

収率 95.0%

溶媒

ethyl acetate

diethyl ether

diethyl ether

反応条件

後処理

1. 1
   workup.ADDITIONadded to the reaction dropwise over 3 minutes
2. 2
   workup.ADDITIONwere added
3. 3
   その他The organic layer was collected
4. 4
   洗浄washed with brine (350 mL)
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo

実験手順

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.

出典