Gallic Acid → phenyl gallate

HRID 1074906Notes

Reaction equation

HRID 1074906 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.[C:13]1(O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P(Cl)(Cl)(Cl)=O>CCOCC>[C:1]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1

Participants

5

Reactant 3

HCID 370Gallic AcidHCID 996PhenolHCID 24813Phosphorus oxychloride

Product 1

HCID 333279phenyl gallate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A reaction mixture was prepared containing 15 g. of anhydrous gallic acid, 8 g. of phenol, 4 ml. of phosphorous oxychloride and 200 ml. of anhydrous ether in a round-bottom flask. The mixture was heated to refluxing temperature for about 18 hours. The ether solvent was removed by evaporation. Water was added to the resulting residue and the pH of the aqueous layer adjusted to about 5 by the addition of dilute aqueous sodium hydroxide. Phenyl gallate, being insoluble at pH=5, separated and was extracted with ether. The ether extracts were separated and dried and the ether removed therefrom by evaporation. Recrystallization of the residue yielded phenyl gallate melting at about 190°-191° C.

Workup

  1. customA reaction mixture was prepared
  2. additioncontaining 15 g
  3. temperatureThe mixture was heated
  4. temperatureto refluxing temperature for about 18 hours
  5. customThe ether solvent was removed by evaporation
  6. additionWater was added to the resulting residue
  7. additionthe pH of the aqueous layer adjusted to about 5 by the addition of dilute aqueous sodium hydroxide
  8. customseparated
  9. extractionwas extracted with ether
  10. customThe ether extracts were separated
  11. customdried
  12. customthe ether removed
  13. customby evaporation
  14. customRecrystallization of the residue

Sources & evidence

ORD record
ord-01d601ada6684110882ba2380ac8c727
Source dataset
uspto-grants-1983_07
Patent number
US04394389

Reaction notes

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