Gallic Acid → Exifone

HRID 597741

Reaction equation

HRID 597741 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.[C:13]1([CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[C:15]=1[OH:16])[OH:14].P(Cl)(Cl)(Cl)=O.[Cl-].[Ca+2].[Cl-]>[Cl-].[Zn+2].[Cl-].O>[OH:14][C:13]1[C:15]([OH:16])=[C:17]([OH:18])[CH:19]=[CH:20][C:21]=1[C:1]([C:2]1[CH:3]=[C:4]([OH:5])[C:6]([OH:7])=[C:8]([OH:9])[CH:10]=1)=[O:12]

Participants

7

Reactant 4

HCID 370Gallic AcidHCID 1057PyrogallolHCID 24813Phosphorus oxychlorideHCID 5284359Calcium Chloride

Product 1

HCID 40399Exifone

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

A reaction of the Fries type was used: ##STR4## 32 g of Gallic acid, 32 g of pyrogallol, 55 g of anhydrous zinc chloride and 100 cm3 of phosphorus oxychloride were mixed in a balloon flask equipped with a condenser and an ampoule of calcium chloride, and were heated to 80° C for 2 hours. After cooling the reaction mixture, a mixture of water and ice was added, whereupon the reaction product precipitated. The reaction product was washed once with water, treated with a solution of sodium bicarbonate, then washed again with water, and finally recrystallised from aqueous solution. Yield: 15 g of crystalline 2,3,3',4,4',5'-hexahydroxybenzophenone having a melting point of 270° C.

Workup

  1. customA reaction of the Fries type
  2. customequipped with a condenser
  3. temperatureAfter cooling the reaction mixture
  4. additionwas added, whereupon the reaction product
  5. customprecipitated
  6. washThe reaction product was washed once with water
  7. additiontreated with a solution of sodium bicarbonate
  8. washwashed again with water
  9. customfinally recrystallised from aqueous solution

Sources & evidence

ORD record
ord-705586672b5542669194ecbf35011dde
Source dataset
uspto-grants-1977_03
Patent number
US04015017

Linked notes

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