Sodium Hydroxide → 2-{4-[(4-Chloroanilino)methyl]phenoxy}-2-methylpropanoic acid

HRID 2058089Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([NH:6][CH2:7][C:8]2[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([OH:16])=[O:15])=[CH:21][CH:22]=2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6.14 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate, 130 ml of 95% ethanol and 52 ml of 1 N aqueous solution of sodium hydroxide is stirred at 70° C. for 50 minutes. After concentrating the reaction mixture under reduced pressure, the residue is dissolved in water and the solution is washed with ether five times. To the aqueous solution is added 55 ml of 1 N hydrochloric acid with cooling, and the precipitated crystals are extracted twice with ether. The extract is washed with water twice, then dried over magnesium sulfate and thereafter the solvent is distilled off to give 5.6 g of 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionic acid, colorless crystals, mp 155° to 158° C.

Workup

concentrationAfter concentrating the reaction mixture under reduced pressure
dissolutionthe residue is dissolved in water
washthe solution is washed with ether five times
additionTo the aqueous solution is added 55 ml of 1 N hydrochloric acid
temperaturewith cooling
extractionthe precipitated crystals are extracted twice with ether
washThe extract is washed with water twice
dry with materialdried over magnesium sulfate
distillationthe solvent is distilled off

Sources & evidence

ORD record: ord-c7b06c8273cf4097b4f0f90b13bf6e59
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04214094

Reaction notes

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