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

HRID 2058091Notes

Reaction equation

HRID 2058091 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19]CC)=[O:18])=[CH:13][CH:12]=2)[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]([CH3:22])([CH3:23])[C:17]([OH:19])=[O:18])=[CH:24][CH:25]=2)[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20329844ethyl 2-[4-{N-(4-chlorophenyl)-N-methylaminomethyl}phenoxy]-2-methylpropionate

Product 1

HCID 203298602-[4-{N-(4-chlorophenyl)-N-methylaminomethyl}phenoxy]-2-methylpropionic acidYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol is dissolved 1.2 g of ethyl 2-[4-{N-(4-chlorophenyl)-N-methylaminomethyl}phenoxy]-2-methylpropionate. Subsequently, 15 ml of 1 N aqueous solution of sodium hydroxide is added to the solution, and the mixture is stirred at room temperature for 4 hours. After distilling off the ethanol from the reaction mixture under reduced pressure, the residue is dissolved in water. The solution is adjusted to pH 4 with 10% hydrochloric acid, and the precipitated crystals are collected by filtration and dried to give 0.94 g of 2-[4-{N-(4-chlorophenyl)-N-methylaminomethyl}phenoxy]-2-methylpropionic acid, mp 63° to 65° C.

Workup

  1. distillationAfter distilling off the ethanol from the reaction mixture under reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. filtrationthe precipitated crystals are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e9885f5d0869494db556ad50fa0b5b4e
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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