Protocatechuic Acid → Benzyl 3,4-dihydroxybenzoate

HRID 234139

Reaktionsgleichung

Reaktionsgleichung von HRID 234139
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 72Protocatechuic AcidHCID 244Benzyl Alcohol2×HCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 16656541Benzyl 3,4-dihydroxybenzoateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To the solution of 3,4-dihydroxybenzoic acid (1.13 g) in benzene (50 ml) were added benzyl alcohol (3.8 ml) and p-toluenesulfonic acid (139 mg), and the mixture was heated at reflux in the presence of Molecular Sieves 4A for 2 days. Further amount of benzyl alcohol (1.5 ml) was added. The mixture was then heated at reflux overnight. After cooling by standing, saturated aqueous sodium hydrogen carbonate was added. The mixture was extracted with ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed by distillation, the residue was dissolved in ethyl acetate and extracted with 1N sodium hydroxide. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with brine, dried over anhydrous magnesium sulfate, the solvent was removed by distillation. The residue was purified by column chromatography on silica gel with an eluent system of chloroform:methanol=30:1 to give 953 mg of benzyl 3,4-dihydroxybenzoate (yield, 53%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was then heated
  3. temperatureat reflux overnight
  4. temperatureAfter cooling
  5. extractionThe mixture was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter the solvent was removed by distillation
  9. dissolutionthe residue was dissolved in ethyl acetate
  10. extractionextracted with 1N sodium hydroxide
  11. extractionextracted with ethyl acetate
  12. washAfter the organic layer was washed with brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customthe solvent was removed by distillation
  15. customThe residue was purified by column chromatography on silica gel with an eluent system of chloroform

Quellen und Nachweise

ORD-Eintrag
ord-abf98f2b22b647588b52d1c6f397b5d9
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594004

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