반응 #1914820

반응 방정식

acetyl chloride

aluminum trichloride

3-iodotoluene

→

title product

수율 51.2%

2-Acetyl-5-iodotoluene

수율 51.2%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred overnight under Argon
2. 2
   기타Organic layer was separated
3. 3
   세척washed once with the saturated ammonium chloride solution
4. 4
   세척washed once with 10% sodium thiosulfate solution
5. 5
   건조dried over sodium sulfate
6. 6
   기타After removing the solvent
7. 7
   workup.DISSOLUTIONthe residue was dissolved in hexane for the column purification
8. 8
   세척the column was eluted with 750 mL of hexane, 750 mL of 1% v/v ether/hexane, 750 mL of 2% v/v ether/hexane and 1500 mL of 3% v/v ether/hexane
9. 9
   workup.ADDITIONThe fractions containing the right isomer
10. 10
    농축concentrated to dryness

실험 절차

To a suspension of 20 gm of aluminum trichloride in 500 mL of dichloromethane was added 10.2 mL of acetyl chloride under Argon. After the reaction mixture was stirred for 15 min, 3-iodotoluene (20 gm) was added through a syringe. The mixture was stirred overnight under Argon and poured into 500 gm of ice-water. Organic layer was separated and washed once with the saturated ammonium chloride solution, and washed once with 10% sodium thiosulfate solution and dried over sodium sulfate. After removing the solvent, the residue was dissolved in hexane for the column purification. Silica gel (260 gm) was packed with hexane, after loading the sample solution, the column was eluted with 750 mL of hexane, 750 mL of 1% v/v ether/hexane, 750 mL of 2% v/v ether/hexane and 1500 mL of 3% v/v ether/hexane. The fractions containing the right isomer were identified by GC-MS and 1H NMR and pooled and concentrated to dryness to afford 12.2 gm (51.2%) of the title product (P 1).

출처