Sodium Hydroxide → HCID 20394400, compound

HRID 261510Notes

Reaction equation

HRID 261510 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([OH:16])[C:12]([O:14]C)=[O:13].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([OH:16])[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54370809HCID 54370809, compound

Product 1

HCID 20394400HCID 20394400, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 13.0 g of methyl 2-(2,6-dichloroanilino)-phenylglycolate in 150 ml of ethanol were added 10 ml of a 5 N aqueous sodium hydroxide solution and the reaction was effected at 80° C. under a nitrogen stream for 1 hour. The ethanol was distilled off under reduced pressure and the residual liquid was diluted with 100 ml of cold water and acidified with a 10% aqueous hydrochloric acid solution. The solid thus deposited was extracted with ether, and the ether extract was washed with water, dried over anhydrous sodium sulfate and then the ether was distilled off at room temperature under reduced pressure. The residue was recrystallized from ether-petroleum ether to give 10.1 g of 2-(2,6-dichloroanilino)phenylglycolic acid. m.p. 140°-142° C. Yield: 81% of theoretical amount.

Workup

  1. customwas effected at 80° C. under a nitrogen
  2. customfor 1 hour
  3. distillationThe ethanol was distilled off under reduced pressure
  4. additionthe residual liquid was diluted with 100 ml of cold water
  5. extractionThe solid thus deposited was extracted with ether
  6. extractionthe ether extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe ether was distilled off at room temperature under reduced pressure
  10. customThe residue was recrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-0e5dea700c284740abf847d75db17623
Source dataset
uspto-grants-1979_08
Patent number
US04166128

Reaction notes

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