Methanol → 3-Oxo-cyclopentanecarboxylic acid methyl ester

HRID 355263

Reaktionsgleichung

Reaktionsgleichung von HRID 355263
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(=O)(=O)(O)O.[CH3:15]O>>[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:15])=[O:8])[CH2:3]1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2277983-Oxocyclopentanecarboxylic acid

Produkt 1

HCID 2376403-Oxo-cyclopentanecarboxylic acid methyl esterAusbeute 84 %

Versuchsvorschrift

A solution of 3-oxocyclopentanecarboxylic acid (13.2 g, 103 mmol), MeOH (130 ml) and 98% sulfuric acid (0.1 ml) was heated under reflux with stirring for 1.5 h. The MeOH was evaporated in vacuo. The residue was dissolved in CH2Cl2 (100 ml) and was washed with 1% sodium bicarbonate (50 ml). The solvent was evaporated in vacuo to give the title compound as a liquid, 12.2 g (84% yield); ir (liq.) νmax : 1730-1740 cm-1 ; 1Hmr (CDCl3) δ: 3.71 (s, 3H, OMe), 3.2 (m, 1H, H-1) and 2.5-1.9 ppm (m, 6H, CH2).

Aufarbeitung

  1. temperatureunder reflux
  2. customThe MeOH was evaporated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (100 ml)
  4. washwas washed with 1% sodium bicarbonate (50 ml)
  5. customThe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cdedfc555b254aa79b635d237cdd2b9c
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04378314

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