Réaction #417920

ord-be31ca51da0a459aac943398e0ead6c1

Équation de réaction

[Na+].[OH-]
sodium hydroxide
CCCCCC/C=C\CCCOc1cccc(C(=O)OC)c1
15
CCCCCC/C=C\CCCOc1cccc(C(=O)OC)c1
methyl 3-(undec-4Z-enyloxy)benzoate
[Na+].[OH-]
sodium hydroxide
→
CCCCCC/C=C\CCCOc1cccc(C(=O)O)c1
yellow oil
Rendement 96.0%
CCCCCC/C=C\CCCOc1cccc(C(=O)O)c1
3-(undec-4Z-enyloxy)benzoic acid
Rendement 96.0%

Réactifs

[Na+].[OH-]
sodium hydroxide
CCCCCC/C=C\CCCOc1cccc(C(=O)OC)c1
15
CCCCCC/C=C\CCCOc1cccc(C(=O)OC)c1
methyl 3-(undec-4Z-enyloxy)benzoate
[Na+].[OH-]
sodium hydroxide

Réactifs

Aucun

Solvants

CO
methanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureThe solution is refluxed overnight
  2. 2
    Températurethe mixture is refluxed for a further 1 hour 30 minutes
  3. 3
    AutreAfter evaporating off the solvent
  4. 4
    Extractionextracted with DCM

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08877684B2uspto-grants-2014_11