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

HRID 1797221Notes

Reaction equation

HRID 1797221 reaction equation
[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

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 728713-Benzoylpropionic acid

Product 1

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

Procedure

To a 1.0 L round bottom flask was added 89 g (0.5 mol) of 3-benzoylpropionic acid and 200 mL of methanol. The solution was 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. 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 96 g; yield 100%; >97% cp. Lit 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.

Workup

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

Sources & evidence

ORD record
ord-6cee1b61779d4768adeaccf55f607aa4
Source dataset
uspto-grants-2006_04
Patent number
US07034059B2

Reaction notes

Loading…