2,6-Dihydroxybenzoic Acid → 2,6-Diacetoxybenzoic acid

HRID 1267827Notes

Reaction equation

HRID 1267827 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([OH:6])=[O:5]>CC(OC(C)=O)=O.OS(O)(=O)=O>[C:2]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:7](=[O:11])[CH3:8])[C:3]=1[C:4]([OH:6])=[O:5])(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 93382,6-Dihydroxybenzoic Acid

Product 1

HCID 100074062,6-Diacetoxybenzoic acidYield 162.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2,6-dihydroxybenzoic acid (4.72 g, 30 mmol) in Ac2O (16 g, 14.2 mL) containing 5 drops of conc. H2SO4 was heated with stirring at 80° for 2 hr until tlc analysis indicated the reaction was complete. The solution was poured onto ice/H2O and extracted 3× with EtOAc. The combined organic phases were washed 4× with H2O and once with brine prior to drying over Na2SO4. After removal of the volatiles using a rotary evaporator, 5.8 g of 2,6-diacetoxybenzoic acid was obtained as a white solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. additionThe solution was poured onto ice/H2O
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic phases were washed 4× with H2O
  5. dry with materialonce with brine prior to drying over Na2SO4
  6. customAfter removal of the volatiles
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-10a7ef1656d4431e99bfd2cc237a2e72
Source dataset
uspto-grants-2003_04
Patent number
US06555519B2

Reaction notes

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