Pyridine → Methyl 3-acetyl-4-(2'-isopropoxy-5'-methyl-benzoyloxy)-benzoate

HRID 236700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236700
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[CH:15]([O:18][C:19]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:20]=1[C:21](Cl)=[O:22])([CH3:17])[CH3:16].N1C=CC=CC=1>O1CCOCC1>[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][C:21](=[O:22])[C:20]1[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:19]=1[O:18][CH:15]([CH3:16])[CH3:17])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 12332833Methyl 3-acetyl-4-hydroxybenzoateHCID 213157482-Isopropoxy-5-methyl-benzoyl chloride

Produkt 1

HCID 21315729Methyl 3-acetyl-4-(2'-isopropoxy-5'-methyl-benzoyloxy)-benzoateAusbeute 113,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Methyl 3-acetyl-4-hydroxy-benzoate (6 g) in dioxane (100 ml) was reacted with 2-isopropoxy-5-methyl-benzoyl chloride (10 g) in the presence of pyridine (10 ml) at room temperature for 16 hours. After dilution with water, the precipitate was extracted with ethyl acetate and the organic solution was washed with 5% NaHCO3 and water and then evaporated to dryness to give methyl 3-acetyl-4-(2'-isopropoxy-5'-methyl-benzoyloxy)-benzoate (13 g, oil), which was dissolved in methyl-ethyl-ketone (200 ml) and treated with anhydrous potassium carbonate (22 g) under stirring at the reflux temperature for 4 hours.

Aufarbeitung

  1. extractionAfter dilution with water, the precipitate was extracted with ethyl acetate
  2. washthe organic solution was washed with 5% NaHCO3 and water
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-0b2b14dab56d4bab94d63009b1de3844
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04157334

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