Sodium Chloride → 2-[(4-methoxycarbonylphenoxy)methyl]benzoic Acid

HRID 1196982Notes

Reaction equation

HRID 1196982 reaction equation
[Na].[CH3:2][O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)=[O:5].[C:13]1([C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][O:15]1)=[O:14].[Cl-].[Na+]>C(O)(=O)C>[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=2[C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6885PhthalideHCID 7456MethylparabenHCID 5360545Sodium

Product 1

HCID 109790172-[(4-methoxycarbonylphenoxy)methyl]benzoic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

In this example, 348.9 g of sodium salt of methyl p-hydroxybenzoate, 402.4 g of phthalide and 200 g of sodium chloride are mixed with one another and stirred at 150° C. for 6 hours. After completion of the reaction, the mixture is cooled until the temperature is brought back to room temperature, 4 l of aqueous 10% acetic acid solution is added thereto and the mixture is allowed to stand at room temperature overnight. After stirring the mixture at room temperature for 3 hours, deposited crystals are separated by filtration, and 6 l of water is added thereto. After stirring the mixture at room temperature for 30 minutes, the deposited crystals are separated by filtration. After the addition of 3 l of toluene to the crystals, the mixture is stirred at room temperature for one hour. The crystals are separated by filtration and dried over heating under reduced pressure to yield 393.9 g of 2-(4-methoxycarbonylphenoxy) methyl benzoic acid.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe mixture is cooled until the temperature
  3. customis brought back to room temperature
  4. waitto stand at room temperature overnight
  5. stirringAfter stirring the mixture at room temperature for 3 hours
  6. customare separated by filtration, and 6 l of water
  7. additionis added
  8. stirringAfter stirring the mixture at room temperature for 30 minutes
  9. customthe deposited crystals are separated by filtration
  10. additionAfter the addition of 3 l of toluene to the crystals
  11. stirringthe mixture is stirred at room temperature for one hour
  12. customThe crystals are separated by filtration
  13. customdried
  14. temperatureover heating under reduced pressure

Sources & evidence

ORD record
ord-701407c5c71a4fd683724f7e3ef6aa88
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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