Reaction #2314283

Reaction equation

HCl

acid chloride

(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetyl chloride

anisole

→

4-Methoxyphenyl (4-(4-methyl-3-pentenyl)-3-cyclohexenyl)methyl ketone

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Temperaturecooled in an ice/ethanol bath
2. 2
   workup.STIRRINGstirred for 30 minutes
3. 3
   ExtractionThe aqueous layer is extracted with dichloromethane
4. 4
   Washthe combined organic layers are sequentially washed with water, sodium bicarbonate, and water
5. 5
   Dryingdried over magnesium sulfate
6. 6
   ConcentrationThe solution is concentrated in vacuo

Procedure

A solution of acid chloride 2C (R=4-Methyl-3-pentenyl) (10 g) in anhydrous dichloromethane (100 mL) is added dropwise to a mixture of ferric chloride (7.8 g) and anisole 2D (4.5 g) in dichloromethane (175 mL), cooled in an ice/ethanol bath. The resulting mixture is gradually warmed to room temperature and stirred overnight. The mixture is poured into 25% HCl (150 mL) and stirred for 30 minutes. The aqueous layer is extracted with dichloromethane, and the combined organic layers are sequentially washed with water, sodium bicarbonate, and water, then dried over magnesium sulfate. The solution is concentrated in vacuo.

Source