Reacción #319115

Ecuación de reacción

ether

4-phenylcyclohexanone

→

4-phenyl-1-methylenecyclohexane

Rendimiento 88.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroa homogeneous solution was formed
2. 2
   workup.ADDITIONAt this point, 1 molar equivalent of TMAL (1.1 milliliter) was added
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 15 minutes
4. 4
   TemperaturaVigorous reflux which
5. 5
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 3 hours
6. 6
   Otroto help separate the organic layer
7. 7
   OtroAfter the usual work up and column separation

Procedimiento

BDAM (3.00 grams) was suspended in 30 milliliters of dry CH2Cl2. Two molar equivalents of ether were added dropwise to the chilled suspension. After about 10 minutes of stirring, a homogeneous solution was formed. At this point, 1 molar equivalent of TMAL (1.1 milliliter) was added. The reaction mixture was stirred at room temperature for 15 minutes and 2.00 grams of 4-phenylcyclohexanone were added. Vigorous reflux which quickly subsided was noticed. The reaction mixture was stirred at room temperature for 3 hours and hydrolyzed as described in Example 1. The aqueous layer was acidified to help separate the organic layer. After the usual work up and column separation, 1.75 grams of 4-phenyl-1-methylenecyclohexane were isolated (88% yield).

Fuente