Potassium Hydroxide → HCID 20298422, compound

HRID 1389214Notes

Reaction equation

HRID 1389214 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([N:8]([CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[K+]>C1C=CC=CC=1.C(O)C>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([N:8]([CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20298374HCID 20298374, compound

Product 1

HCID 20298422HCID 20298422, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

15.0 g of ethyl 4-[p-chloro-N-(biphenyl-2-yl)benzamido]-butyrate is dissolved in 100 ml of benzene and, after the addition thereto of a solution of 2.8 g of potassium hydroxide in 20 ml of ethanol, is then stirred at room temperature for 5 hours. The solvent is then distilled off in vacuo, and the obtained residue is dissolved in water. The resulting aqueous solution is acidified with dilute hydrochloric acid, and the precipitate, which separates out, is taken up in methylene chloride. The residue remaining, after drying and distilling off the methylene chloride, is recrystallized from an ethanol/water mixture (2:1) to obtain 10.1 g (72.1% of theory) of 4-[p-chloro-N-(biphenyl-2-yl)benzamido]butyric acid, MP 135° to 137°.

Workup

  1. additionafter the addition
  2. distillationThe solvent is then distilled off in vacuo
  3. dissolutionthe obtained residue is dissolved in water
  4. customafter drying
  5. distillationdistilling off the methylene chloride
  6. customis recrystallized from an ethanol/water mixture (2:1)

Sources & evidence

ORD record
ord-cc12a4bb562d4831a5ff2547bf3ae8ac
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

Loading…