Reaction #1121718

Reaction equation

acetophenone

4-tert-butylbenzoyl chloride

→

1-phenylvinyl 4-tert-butylbenzoate

Yield 57.0%

Solvents

water

Conditions

Workup

1. 1
   workup.WAITThe mixture was then left
2. 2
   Temperatureto cool
3. 3
   Extractionextracted with dichloromethane
4. 4
   DryingThe organic phase was dried over magnesium sulfate
5. 5
   Otherthe solvent was removed under reduced pressure
6. 6
   OtherA 2.12 g sample was purified by flash chromatography (hexane:dichloromethane 3:1)

Procedure

A mixture of 4.16 g (21.62 mmol) of acetophenone trimethylsilylenol, 4.33 g (22.01 mmol) of 4-tert-butylbenzoyl chloride and 136 mg of mercuric chloride was heated at 100° C. for 2 h. The mixture was then left to cool, water was added over the reaction crude and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. A 2.12 g sample was purified by flash chromatography (hexane:dichloromethane 3:1) giving 1.17 g of 1-phenylvinyl 4-tert-butylbenzoate. Yield 57%.

Source