Methanol → Benzenebutanoic acid, gamma-oxo-, methyl ester

HRID 377949

Reaktionsgleichung

Reaktionsgleichung von HRID 377949
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:19]O>>[C:1]([CH2:9][CH2:10][C:11]([O:13][CH3:19])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 728713-Benzoylpropionic acid

Produkt 1

HCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterAusbeute 100 %

Versuchsvorschrift

To a 1.0 L round bottom flask was added 49.25 g (0.276 mol) of 3-benzoylpropionic acid. To this was added 700 mL of ACS methanol and the solution stirred until all of the acid had dissolved. To this solution was added approximately 2.0 mL of conc. H2SO4 and the reaction refluxed for 2.5 hours. The reaction can be monitored by HPLC. After the reaction was determined to be complete, the methanol was removed on the rotoevaporator and to the residual oil was added ethyl acetate (~500 mL). To the ethyl acetate layer was then added 150 mL of a saturated sodium carbonate solution. The layers were extracted and allowed to separate. The organic layer was then dried (MgSO4), filtered and concentrated to yield methyl 3-benzoylpropionate (1) as a light yellow oil. Yield 53.30 g; yield 100%; >97% cp. Lt bp 172-174° C. at 10 mm Hg.; 1H NMR ppm (δ), CDCl3, 7.98 (dd, 2H), 7.54 (m, 1H), 7.45(m, 2H), 3.70 (s, 3H, OCH3), 3.32 (t, 2H), 2.76 (t, 2H). 13C NMR ppm (δ), CDCl3 198.0 (C=O), 173.3 (CO2), 136.5 (q), 133.2, 128.6, 128.0, 51.7 (OCH3), 33.3, 28.0. IR oil cm-1 2952, 1737, 1687, 1596, 1449, 1358, 1221, 1168, 1001, 750, 691.

Aufarbeitung

  1. dissolutionhad dissolved
  2. temperaturethe reaction refluxed for 2.5 hours
  3. customThe reaction
  4. customthe methanol was removed on the rotoevaporator and to the residual oil
  5. additionwas added ethyl acetate (~500 mL)
  6. additionTo the ethyl acetate layer was then added 150 mL of a saturated sodium carbonate solution
  7. extractionThe layers were extracted
  8. customto separate
  9. dry with materialThe organic layer was then dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c52d7e0021dc419592042d8fcb81d8c6
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028224

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