Reaction #417920

Reaction equation

sodium hydroxide

15

methyl 3-(undec-4Z-enyloxy)benzoate

sodium hydroxide

→

yellow oil

Yield 96.0%

3-(undec-4Z-enyloxy)benzoic acid

Yield 96.0%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureThe solution is refluxed overnight
2. 2
   Temperaturethe mixture is refluxed for a further 1 hour 30 minutes
3. 3
   OtherAfter evaporating off the solvent
4. 4
   Extractionextracted with DCM

Procedure

4 mL of 1 N sodium hydroxide solution (4.0 mmol) are added portionwise to 1.14 g of 15 (3.74 mmol) in methanol (30 mL). The solution is refluxed overnight. A further 4 mL of 1 N sodium hydroxide solution are added, and the mixture is refluxed for a further 1 hour 30 minutes. After evaporating off the solvent, the reaction medium is acidified with 0.5 N HCl and extracted with DCM. 1.04 g of a yellow oil are obtained, i.e. a yield of 96%.

Source