Reaction #939020

Reaction equation

1,2-cyclohexanedicarboxylic anhydride

hexanol

→

cyclohexane-1,2-dicarboxylic acid dihexyl ester

Yield 120.7%

Solvents

heptane

toluene

Conditions

Workup

1. 1
   Temperaturewas refluxed for 3 days
2. 2
   Otherwater removed from the reaction mixture
3. 3
   OtherAfter reaction
4. 4
   Othersolvent was removed in vacuo
5. 5
   Otherto yield a viscous oil

Procedure

A mixture of 1,2-cyclohexanedicarboxylic anhydride (60 g), hexanol (85 g), and p-toluenesulfonic acid (100 mg) in toluene (500 mL) was refluxed for 3 days and water removed from the reaction mixture. After reaction was complete, solvent was removed in vacuo to yield a viscous oil. The crude material was redissolved in heptane and passed through a pad of silica gel to obtain cyclohexane-1,2-dicarboxylic acid dihexyl ester (80 g) as a pale yellow oil.

Source