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

HRID 377949

Reaction equation

HRID 377949 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 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.

Workup

  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

Sources & evidence

ORD record
ord-c52d7e0021dc419592042d8fcb81d8c6
Source dataset
uspto-grants-2000_02
Patent number
US06028224

Linked notes

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