Reaction #54243

Reaction equation

1-bromo-1-phenyl-3,3-dimethyl-butan-2-one

4-chlorophenol

sodium

→

1-phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-one

Yield 67.0%

Solvents

ethyl acetate

ethanol

Conditions

Workup

1. 1
   Temperatureunder reflux
2. 2
   Otherthe sodium bromide which had separated out
3. 3
   Filtrationwas filtered off hot
4. 4
   workup.DISTILLATIONThe filtrate was distilled in vacuo
5. 5
   Otherthe solid residue which remained was recrystallized from ligroin

Procedure

A solution of 25.4 g (0.1 mole) of 1-bromo-1-phenyl-3,3-dimethyl-butan-2-one in 50 ml of ethyl acetate was added dropwise, at the boil, to a solution of 12.85 g (0.1 mole) of 4-chlorophenol and 2.3 g (0.1 mole) of sodium in 100 ml of ethanol. After boiling for 12 hours under reflux, the sodium bromide which had separated out was filtered off hot. The filtrate was distilled in vacuo and the solid residue which remained was recrystallized from ligroin. 20.2 g (67% of theory) of 1-phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-one of melting point 103° C. were obtained.

Source