Reaction #452449

Reaction equation

1-hydroxycyclohexyl 4-(2-carboxyethyl)carbonylphenyl ketone

thionyl chloride

→

1-hydroxycyclohexyl 4-(2-chloroformylethyl)carbonylphenyl ketone

Yield 94.0%

Solvents

diethyl ether

Conditions

Workup

1. 1
   OtherA 250-ml round-bottomed flask fitted with a condenser
2. 2
   OtherThe resulting reaction mixture
3. 3
   Otherafter which time the solvent was removed under reduced pressure
4. 4
   TemperatureThe residue, a white solid, was maintained at 0.01 Torr for 30 minutes
5. 5
   Otherto remove residual solvent and excess thionyl chloride

Procedure

A 250-ml round-bottomed flask fitted with a condenser was charged with 12.0 g of 1-hydroxycyclohexyl 4-(2-carboxyethyl)carbonylphenyl ketone (0.04 mole), 5.95 g (0.05 mole) of thionyl chloride (Aldrich Chemical Co., Milwaukee, Wis.), and 50 ml of diethyl ether. The resulting reaction mixture was stirred at 30° C. for 30 minutes, after which time the solvent was removed under reduced pressure. The residue, a white solid, was maintained at 0.01 Torr for 30 minutes to remove residual solvent and excess thionyl chloride, leaving 12.1 g (94 percent) of 1-hydroxycyclohexyl 4-(2-chloroformylethyl)carbonylphenyl ketone.

Source