Reaction #417924

ord-ee97116ffb3d4ffe8071e8b03e6f1be5

Reaction equation

[Na+].[OH-]
sodium hydroxide
CCCCCC/C=C\CCCOc1ccccc1C(=O)OC
29
CCCCCC/C=C\CCCOc1ccccc1C(=O)OC
methyl 2-(undec-4Z-enyloxy)benzoate
CCCCCC/C=C\CCCOc1ccccc1C(=O)O
yellow oil
Yield 99.5%
CCCCCC/C=C\CCCOc1ccccc1C(=O)O
2-(undec-4Z-enyloxy)benzoic acid
Yield 99.5%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe solution is refluxed for 24 hours
  2. 2
    OtherAfter evaporating off the solvent
  3. 3
    Extractionextracted with DCM

Procedure

500 μL of 1 N sodium hydroxide solution (500 μmol) are added portionwise to 80 mg of 29 (263 μmol) in methanol (3 mL). The solution is refluxed for 24 hours. After evaporating off the solvent, the reaction medium is acidified with 0.5 N HCl and extracted with DCM. 76 mg of a yellow oil are obtained, i.e. a yield of 99%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877684B2uspto-grants-2014_11