Water → 2,4-Bis(2-methoxybenzamido)benzoic acid

HRID 1606640Notes

Reaction equation

HRID 1606640 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[C:5]([NH:7][C:8]1[CH:17]=[C:16]([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH:15]=[CH:14][C:9]=1[C:10]([O:12]C)=[O:11])=[O:6].O1CCOCC1.[OH-].[K+].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[C:5]([NH:7][C:8]1[CH:17]=[C:16]([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH:15]=[CH:14][C:9]=1[C:10]([OH:12])=[O:11])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 13066651HCID 13066651, compound

Product 1

HCID 130666522,4-Bis(2-methoxybenzamido)benzoic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5 g of methyl 2,4-bis(2'-methoxybenzamido)-benzoate obtained in Example 9 was admixed with 250 ml of dioxane, 3 g of potassium hydroxide and 50 ml of water, followed by stirring the mixture at room temperature for 20 to 30 hours. The mixture was then poured into 1.5 l of ice-water containing 20 ml of acetic acid to precipitate crystals. The crystals were recovered by filtration, washed with water and recrystallized from ethanol-water to yield 3.6 g of 2,4-bis(2'-methoxybenzamido)-benzoic acid having a melting point between 232° - 233°C.

Workup

  1. customto precipitate crystals
  2. filtrationThe crystals were recovered by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-fc3f9c787c4d4cbca3a54eb06ce2ca7f
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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