4-Hydroxybenzoic Acid → 4,4'-[1,3-Phenylenebis(carbonyloxy)]dibenzoic acid

HRID 1657149Notes

Reaction equation

HRID 1657149 reaction equation
[OH-:1].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[OH2:13].[C:14](Cl)(=[O:24])[C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([C:18](Cl)=[O:19])[CH:16]=1>C(Cl)Cl>[C:8]([C:7]1[CH:11]=[CH:12][C:4]([O:3][C:14](=[O:24])[C:15]2[CH:23]=[CH:22][CH:21]=[C:17]([C:18]([O:1][C:4]3[CH:12]=[CH:11][C:7]([C:8]([OH:9])=[O:13])=[CH:6][CH:5]=3)=[O:19])[CH:16]=2)=[CH:5][CH:6]=1)([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 962WaterHCID 7451Isophthaloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 705510914,4'-[1,3-Phenylenebis(carbonyloxy)]dibenzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 liter three-necked Morton flask equipped with nitrogen inlet and outlet, thermometer, condenser and mechanical stirrer, were placed 179.6 grams (4.4 moles) of sodium hydroxide, 289.8 grams (2.1 m) of p-hydroxybenzoic acid, and 3 liters of distilled water. Isophthaloyl dichloride (203 grams, 1 m) was dissolved in 3 liters of methylene chloride. The acid chloride solution was added into the reaction flask with fast agitation. The resulting mixture was stirred at room temperature for one hour, and the solid disodium salt of the product was filtered, washed with water, and then acidified with a 10% solution of hydrochloric acid. The crude product was filtered, washed three times with distilled water, and twice with hot methanol, and then dried at 100° C. to obtain 300 grams of di(p-carboxyphenyl)isophthalate in 74% yield, with a melting point of 290°-300° C.

Workup

  1. customIn a 10 liter three-necked Morton flask equipped with nitrogen inlet and outlet
  2. customthermometer, condenser and mechanical stirrer, were placed
  3. filtrationthe solid disodium salt of the product was filtered
  4. washwashed with water
  5. filtrationThe crude product was filtered
  6. washwashed three times with distilled water
  7. dry with materialtwice with hot methanol, and then dried at 100° C.

Sources & evidence

ORD record
ord-afa6f8b5af5048b09ae2724386e589cb
Source dataset
uspto-grants-1993_10
Patent number
US05256760

Reaction notes

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