Water → HCID 12852271, compound

HRID 1156213Notes

Reaction equation

HRID 1156213 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[OH:10].[N+]([C:14]1[CH:15]=[C:16]([C:24]([O:26][CH3:27])=[O:25])[C:17](=[CH:22][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19])([O-])=O.O>CN(C)C=O>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[O:10][C:23]1[CH:22]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[C:16](=[CH:15][CH:14]=1)[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 84492,4-DichlorophenolHCID 691191,2-Benzenedicarboxylic acid, 4-nitro-, 1,2-dimethyl esterHCID 5360545Sodium

Product 1

HCID 12852271HCID 12852271, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.4 g (0.012 mole) of sodium salt of 2,4-dichlorophenol and 2.4 g (0.010 mole) of dimethyl 4-nitrophthalate are dissolved in dry dimethylformamide and stirred at 130°-150° C. for 5 hours. After cooling, the mixture is poured into cold water, extracted with benzene, successively washed with dilute aqueous caustic soda, dilute hydrochloric acid and water, dried over sodium sulfate and then concentrated to obtain 2.5 g of an oily product. It was purified by column chromatography and there was obtained 1.6 g of the intended compound as a viscous oily product. Yield 45%.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with benzene
  3. washsuccessively washed with dilute aqueous caustic soda, dilute hydrochloric acid and water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d11a6d5b290441b866ba546759ada78
Source dataset
uspto-grants-1982_06
Patent number
US04334915

Reaction notes

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