Phthalic Anhydride → 2-(2-Hydroxy-4-pyrrolidinylbenzoyl)benzoic acid

HRID 980976Notes

Reaction equation

HRID 980976 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[N:12]1([C:17]2[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1>ClCCCl>[OH:23][C:19]1[CH:18]=[C:17]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:22]=[CH:21][C:20]=1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 1176643-(1-Pyrrolidinyl)phenol

Product 1

HCID 64521652-(2-Hydroxy-4-pyrrolidinylbenzoyl)benzoic acidYield 36.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 14.8 g (0.1 mole) of phthalic anhydride, 16.3 g (0.1 mole) of 100 percent 3-pyrrolidinophenol and 50.0 ml of 1,2-dichloroethane was maintained at approximately 40° C. for approximately twenty-four hours, at approximately 60° C. for approximately twenty-four hours and at reflux temperature for approximately twelve hours. After cooling the reaction mixture to ambient temperature, the solid which precipitated was collected by filtration and washed with 500.0 ml of 1,2 dichloroethane. The solid was dissolved in dilute aqueous soduim hydroxide, the resulting mixture was filtered to remove insolubles. The filtrate was adjusted to pH 7.0 with the addition of glacial acetic acid and the solid tar-like material which formed was collected by filtration. To the filtrate, an additional amount of glacial acetic acid was added. The solid which precipitated was collected by filtration, washed with water and dried to obtain 11.3 g of 2-(2-hydroxy-4-pyrrolidinophenyl)carbonylbenzoic acid, a pale pink-colored solid which melted at 190° to 192° C. To the filtrate, there was added an additional portion of glacial acetic acid and the solid which was collected by filtration, washed with water and dried to obtain 0.3 g of pale yellow-colored crystals of the desired product which melted at 193° to 195° C. The infrared spectra of the two solids were identical having significant maxima at 1100 cm-1 (C=O;m). The nuclear magnetic spectra were consistent with the assigned structure.

Workup

  1. temperatureat reflux temperature for approximately twelve hours
  2. temperatureAfter cooling the reaction mixture to ambient temperature
  3. customthe solid which precipitated
  4. filtrationwas collected by filtration
  5. washwashed with 500.0 ml of 1,2 dichloroethane
  6. dissolutionThe solid was dissolved in dilute aqueous soduim hydroxide
  7. filtrationthe resulting mixture was filtered
  8. customto remove insolubles
  9. additionThe filtrate was adjusted to pH 7.0 with the addition of glacial acetic acid
  10. customthe solid tar-like material which formed
  11. filtrationwas collected by filtration
  12. additionTo the filtrate, an additional amount of glacial acetic acid was added
  13. customThe solid which precipitated
  14. filtrationwas collected by filtration
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-dc2ba5211ab1488dabdd6031d199fba0
Source dataset
uspto-grants-1987_01
Patent number
US04639750

Reaction notes

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