Reaction #2314292

Reaction equation

isoprene

pentylbutadiene

vinyl acetate

aluminum chloride

→

4-Methyl-3-cyclohexenol acetate

Solvents

toluene

Conditions

Workup

1. 1
   workup.WAITto stand at 4° C. for a further 16 hours
2. 2
   ExtractionThe reaction mixtire is then sequentially extracted with two portions (150 mL each) of 1% hydrochloric acid solution, water (75 mL), and brine (75 mL)
3. 3
   DryingIt is dried over sodium sulfate
4. 4
   Filtrationfiltered through Celite
5. 5
   Concentrationconcentrated in vacuo
6. 6
   workup.DISTILLATIONThe product is distilled
7. 7
   Otherto give 30 g of clear, colorless liquid

Procedure

To a solution of vinyl acetate 4A (20 mL) in anhydrous toluene (220 mL) is added aluminum chloride (2.89 g). The flask is cooled to 0° C., and the isoprene 1C (R=methyl) (21.7 mL) is added dropwise. The reaction mixture is stirred 5 hours at 0° C., then allowed to stand at 4° C. for a further 16 hours. The reaction mixtire is then sequentially extracted with two portions (150 mL each) of 1% hydrochloric acid solution, water (75 mL), and brine (75 mL). It is dried over sodium sulfate, filtered through Celite, and concentrated in vacuo. The product is distilled to give 30 g of clear, colorless liquid.

Source