반응 #465131

반응 방정식

3-benzoylpropionic acid

H2SO4

methanol

→

methyl 3-benzoylpropionate

수율 100.0%

반응 조건

후처리

1. 1
   workup.DISSOLUTIONhad dissolved
2. 2
   온도the reaction refluxed for 2.5 hours
3. 3
   기타The reaction
4. 4
   기타the methanol was removed on the rotoevaporator and to the residual oil
5. 5
   workup.ADDITIONwas added ethyl acetate (~500 mL)
6. 6
   workup.ADDITIONTo the ethyl acetate layer was then added 150 mL of a saturated sodium carbonate solution
7. 7
   추출The layers were extracted
8. 8
   기타to separate
9. 9
   건조The organic layer was then dried (MgSO4)
10. 10
    여과filtered
11. 11
    농축concentrated

실험 절차

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.

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