Reaction #1914820

Reaction equation

acetyl chloride

aluminum trichloride

3-iodotoluene

→

title product

Yield 51.2%

2-Acetyl-5-iodotoluene

Yield 51.2%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred overnight under Argon
2. 2
   OtherOrganic layer was separated
3. 3
   Washwashed once with the saturated ammonium chloride solution
4. 4
   Washwashed once with 10% sodium thiosulfate solution
5. 5
   Dryingdried over sodium sulfate
6. 6
   OtherAfter removing the solvent
7. 7
   workup.DISSOLUTIONthe residue was dissolved in hexane for the column purification
8. 8
   Washthe 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
    Concentrationconcentrated to dryness

Procedure

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).

Source