Benzene → HCID 20350648, compound

HRID 1449238Notes

Reaction equation

HRID 1449238 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:23]([O:25]C)=[O:24])[C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])=[CH:4][CH:3]=1.C1C=CC=CC=1.[OH-].[Na+].Cl>CCOCC.O.C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:23]([OH:25])=[O:24])[C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20350646HCID 20350646, compound

Product 1

HCID 20350648HCID 20350648, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

The mixture of 4.3 g of methyl N-(p-methylbenzyl)-o-(2,6-dichloroanilino)phenylacetate, 8 ml of benzene, 5 ml of ethanol, 8 ml of water and 2.5 g of 98% sodium hydroxide was refluxed for 8 hours under thoroughly stirring. After cooling the reaction mixture, 10% HCl aq. sol. was added to adjust pH 2 to 3 and 30 ml of ether was added and the ether phase was separated. The ether solution was dried over anhydrous sodium sulfate and the solvent was distilled off and the residue was recrystallized from ether-hexane to obtain 3.4 g of N-(p-methylbenzyl)-o-(2,6-dichloroanilino)phenylacetic acid as colorless crystals. Yield: 85%

Workup

  1. temperaturewas refluxed for 8 hours
  2. additionwas added
  3. additionwas added
  4. customthe ether phase was separated
  5. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-eeda4c9f05114844afa9b4451203f322
Source dataset
uspto-grants-1980_02
Patent number
US04189595

Reaction notes

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