Sodium Hydroxide → 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionic acid

HRID 2058092Notes

Reaction equation

HRID 2058092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:16][C:17]2[CH:31]=[CH:30][C:20]([O:21][C:22]([CH3:29])([CH3:28])[C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:21][C:22]([CH3:28])([CH3:29])[C:23]([OH:25])=[O:24])=[CH:30][CH:31]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20329839ethyl 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionate

Product 1

HCID 203298412-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionic acidYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 40 ml of ethanol is dissolved 2.3 g of ethyl 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionate, and 25 ml of 1 N aqueous solution of sodium hydroxide is added to the solution. The mixture is refluxed under heating for 2 hours. After concentrating the reaction mixture under reduced pressure, the residue is dissolved in water. The solution is adjusted to pH 4 with 10% hydrochloric acid. The resulting crystals are collected by filtration and dried to give 1.9 g of 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionic acid, mp 65° to 67° C.

Workup

  1. additionis added to the solution
  2. temperatureThe mixture is refluxed
  3. temperatureunder heating for 2 hours
  4. concentrationAfter concentrating the reaction mixture under reduced pressure
  5. dissolutionthe residue is dissolved in water
  6. filtrationThe resulting crystals are collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-5143576ac6d54935a5684fef1baa43b0
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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