Reaction #2358534

ord-12ca1f495cc94f539bbe45bf7ed52fad

Reaction equation

Cl
HCl
CCOC(=O)c1cccc(C#CCCCC(=O)N(C)C)c1
3-(5-Dimethylcarbamoyl-pent-ynyl)benzoic acid ethyl ester
[Na+].[OH-]
sodium hydroxide
→
CN(C)C(=O)CCCC#Cc1cccc(C(=O)O)c1
3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid
Yield 74.0%
CN(C)C(=O)CCCC#Cc1cccc(C(=O)O)c1
3-(5-Dimethylcarbamoyl-pent-1-ynyl)-benzoic acid
Yield 74.0%

Reactants

Cl
HCl
CCOC(=O)c1cccc(C#CCCCC(=O)N(C)C)c1
3-(5-Dimethylcarbamoyl-pent-ynyl)benzoic acid ethyl ester
[Na+].[OH-]
sodium hydroxide
—
solution

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe solvent was removed under vacuum
  2. 2
    OtherThe residue was triturated with ethyl acetate

Procedure

3-(5-Dimethylcarbamoyl-pent-ynyl)benzoic acid ethyl ester (0.800 g, 2.78 mmol) was treated with sodium hydroxide 1M solution (6 mL) overnight. To the reaction mixture 7 mL of HCl 1M solution was added and the solvent was removed under vacuum. The residue was triturated with ethyl acetate, to give 3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid (24) (0.590 g, 2.05 mmol; yield 74%) as white off powder.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120723B2uspto-grants-2015_09