반응 #430249

반응 방정식

aluminum chloride

ethanol

acetyl chloride

2-chloroanisole

→

3-chloro-4-methoxyacetophenone

수율 76.0%

용매

water

chloroform

chloroform

반응 조건

후처리

1. 1
   workup.ADDITIONwas added over 25 minutes
2. 2
   기타The phases were separated
3. 3
   추출the aqueous phase was extracted with dichloromethane
4. 4
   건조The combined organics were dried over anhydrous MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타to afford a solid which
8. 8
   기타was crystallized from dichloromethane/hexane

실험 절차

Anhydrous aluminum chloride (281 g, 2.104 mol) and 1 L of ethanol-free chloroform were maintained at 0° C. with an ice bath while a solution of acetyl chloride (162 g, 2.28 mol) in 300 mL of chloroform was added over 25 minutes. To this solution was added 2-chloroanisole (250 g, 1.75 mol) in 250 mL of chloroform over 1 hour. The solution was stirred at room temperature for 16 hours and was poured into a mixture of ice and water. The phases were separated and the aqueous phase was extracted with dichloromethane and combined with the original organic phase. The combined organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford a solid which was crystallized from dichloromethane/hexane to give 3-chloro-4-methoxyacetophenone (246 g, 76%) which was used directly in the next step without further purification.

출처