Reaction #939018

Reaction equation

sulfuric acid

butyl iodide

iodine

adipic acid monoethyl ester chloride

→

Ethyl 6-Oxodecanoate

Solvents

water

toluene

butyl acetate

Conditions

Workup

1. 1
   Otherto react
2. 2
   workup.ADDITIONwas added to the reaction solution
3. 3
   ExtractionThe oily layer was extracted with ether
4. 4
   Washwashed with aqueous sodium hydrogencarbonate
5. 5
   Washwashed with water
6. 6
   Otherdried
7. 7
   OtherThe residue was evaporated
8. 8
   Otherto remove the solvent
9. 9
   workup.DISTILLATIONdistilled

Procedure

A mixture of activated zinc-copper catalyst (11.5 g), butyl acetate (4 g), toluene (5 g), butyl iodide (15 g) and iodine (3 mg) was heated at 110-120° C. for 2 hours. The mixture was then added dropwise with adipic acid monoethyl ester chloride(15.7 g) at 0° C., and then was allowed to react. After the reaction was completed, ice-cooled water was added to the reaction solution, and then decomposed with dilute sulfuric acid. The oily layer was extracted with ether, washed with aqueous sodium hydrogencarbonate, washed with water, and then dried. The residue was evaporated to remove the solvent, and then distilled, thereby giving ethyl 6-oxodecanoate (8.1 g).

Source