Sodium Hydroxide → 2-(4-(2,4-Dichlorophenoxy)phenoxy)propionic acid

HRID 1583657Notes

Reaction equation

HRID 1583657 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C[O:18][C:19](=[O:23])[CH:20](Cl)[CH3:21].[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:20]([CH3:21])[C:19]([OH:23])=[O:18])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 28659Methyl 2-chloropropionateHCID 945094-(2,4-Dichlorophenoxy)phenol

Product 1

HCID 386872-(4-(2,4-Dichlorophenoxy)phenoxy)propionic acid

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred solution of 127.5 parts of 4-(2',4'-dichlorophenoxy)-phenol and 69.2 parts of 2-chloropropionic acid methyl ester in 650 parts of xylene, 100 parts of 50% sodium hydroxide solution are added dropwise at about 110° C. and 500 mbar while simultaneously distilling off the azeotropic mixture of water and methanol. The addition being complete, stirring is continued for 15 minutes at 110° C. Work-up is as described in Example 1. 163.3 Parts of 2-[4'-(2",4"-dichlorophenoxy)-phenoxy]propionic acid are obtained. The content of pure final product is 99.8%, corresponding to 99.6% of theory. The residual amount of 4-(2',4'-dichlorphenoxy)-phenol is 0.15%.

Workup

  1. distillation500 mbar while simultaneously distilling off
  2. additionthe azeotropic mixture of water and methanol
  3. additionThe addition

Sources & evidence

ORD record
ord-5cd6a66ba47a427aa3a8f1373ea3c425
Source dataset
uspto-grants-1985_11
Patent number
US04552977

Reaction notes

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