Reaction #473517

Reaction equation

4-Propyl-cyclohexanecarboxylic acid

4-bromobutan-1-ol

para-toluene sulphonic acid

→

4-propyl-cyclohexanecarboxylic acid 4-bromo-butyl ester

Solvents

toluene

Conditions

Workup

1. 1
   Otherequipped with Dean-Stark apparatus over night
2. 2
   Washis washed with aqueous sodium carbonate and water
3. 3
   Otherdried
4. 4
   Otherevaporated to dryness
5. 5
   OtherPurification
6. 6
   OtherEvaporation of the appropriate fractions

Procedure

4-Propyl-cyclohexanecarboxylic acid (10.0 g, 58.0 mmol), 4-bromobutan-1-ol (9.2 g, 60.0 mmol) and a catalytic amount of para-toluene sulphonic acid are stirred under reflux in toluene (300 ml) in a flask equipped with Dean-Stark apparatus over night. The solution is allowed to cool to room temperature, is washed with aqueous sodium carbonate and water, dried and evaporated to dryness. Purification is achieved by flash column chromatography using petrol as eluant. Evaporation of the appropriate fractions gives 4-propyl-cyclohexanecarboxylic acid 4-bromo-butyl ester as the product. The structure is confirmed by 1H NMR spectroscopy and GCMS.

Source