Benzoic Acid → 4-Acetoxy-3-acetylbenzoic acid

HRID 26718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 26718
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].C(Cl)Cl.[C:17](OC(=O)C)(=[O:19])[CH3:18].C(O)(=O)C1C=CC=CC=1>C(N(CC)CC)C.O1CCCC1>[C:17]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12])(=[O:19])[CH3:18]

Komponenten

7

Edukt 4

HCID 243Benzoic AcidHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 91792453-Acetyl-4-hydroxybenzoic acid

Produkt 1

HCID 213223944-Acetoxy-3-acetylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a suspension of 2.3 g. of 4-hydroxy-3-acetylbenzoic acid in 100 ml. of methylene chloride and 100 ml. of tetrahydrofuran, a mixture of 1.5 g. of triethylamine, 1.6 g. of 4-N-dimethylaminopyridine and 1.5 g. of acetic anhydride is added. The reaction mixture is heated at 50° for one hour. The solution is extracted with ethyl acetate, the organic layer washed with water and dilute hydrochloric acid and evaporated to dryness to yield 2.1 g. of the benzoic acid product. NMR in CDCl3

Aufarbeitung

  1. additionTo a suspension of 2.3 g
  2. temperatureThe reaction mixture is heated at 50° for one hour
  3. extractionThe solution is extracted with ethyl acetate
  4. washthe organic layer washed with water and dilute hydrochloric acid
  5. customevaporated to dryness
  6. customto yield 2.1 g

Quellen und Nachweise

ORD-Eintrag
ord-8565aed6498241c8809f1e76110e1797
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151297

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