Reaction #2314284

Reaction equation

ketone

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

potassium hydroxide

hydrazine hydrate

→

2-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl-4-methoxybenzene

Solvents

diethylene glycol

Conditions

Workup

1. 1
   Temperature150° C., all for 30 minutes each, then cooled to room temperature
2. 2
   ExtractionThe reaction mixture is extracted between ethyl ether and water
3. 3
   Washthe combined organic layers are washed with brine
4. 4
   Dryingdried over magnesium sulfate
5. 5
   ConcentrationThe solution is concentrated in vacuo
6. 6
   Filtrationthe product is purified by silica gel filtration

Procedure

To a solution of ketone 2E (R=4-Methyl-3-pentenyl) (10 g) in diethylene glycol (30 mL) is added potassium hydroxide (4.3 g) and hydrazine hydrate (4.5 mL). The solution is sequentially heated to 100° C., 125° C., and 150° C., all for 30 minutes each, then cooled to room temperature. The reaction mixture is extracted between ethyl ether and water, and the combined organic layers are washed with brine and dried over magnesium sulfate. The solution is concentrated in vacuo, and the product is purified by silica gel filtration using 20:1 hexanes:ethyl acetate as an eluent.

Source