Reaction #2193

Reaction equation

4-chloro-4'-mercaptomethylbenzophenone

ethyl bromide

potassium hydroxide

→

desired product

Yield 79.1%

4-Chloro-4'-ethylthiomethylbenzophenone

Yield 79.1%

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureunder reflux
2. 2
   Concentrationconcentrated
3. 3
   workup.ADDITIONWater was added to the residue
4. 4
   Extractionthe mixture was extracted with ethyl acetate
5. 5
   WashThe ethyl acetate layer was washed with water
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated
8. 8
   OtherThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Procedure

4-chloro-4'-mercaptomethylbenzophenone (16.0 g), ethyl bromide (7.4 g) and potassium hydroxide (4.3 g) were added to methanol (250 ml), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was cooled to room temperature and then concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1) to obtain the desired product 14.0 g, melting point: 33° to 34° C., yield: 79%).

Source