Reaction #54760

Reaction equation

ammonia

4-Methylcyclohexanone

sodium amide

o-chloroanisole

→

2-Methoxyphenyl-4-methylcyclohexanone

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Otherthe ice bath was removed
3. 3
   Temperaturethe mixture was heated
4. 4
   Temperatureat reflux until the evolution of ammonia
5. 5
   Other(~3 hours)
6. 6
   TemperatureWhile still at reflux

Procedure

4-Methylcyclohexanone (224 g, 2 moles) was added dropwise rapidly to a cooled, stirred suspension of 170 g (4 moles) of sodium amide in 2 l of tetrahydrofuran under nitrogen. After the addition was complete, the ice bath was removed and the mixture was heated at reflux until the evolution of ammonia ceased (~3 hours). While still at reflux, 142.5 g (1 mole) of o-chloroanisole was added rapidly dropwise and the mixture was heated for an additional hour, until evolution of ammonia ceased.

Source