Réaction #1994220

Équation de réaction

calcium hydroxide

2,4-dimethylbenzoic acid

sulfuric acid

ethanol

→

1

Rendement 95.0%

Ethyl 2,4-Dimethylbenzoate

Rendement 95.0%

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was refluxed over night
2. 2
   Températurecooled down
3. 3
   FiltrationThe suspension was filtered over celite and
4. 4
   Concentrationconcentrated in vacuo
5. 5
   workup.DISTILLATIONThe crude product was purified by vacuum distillation

Mode opératoire

To a solution of commercially available 2,4-dimethylbenzoic acid (67.8 g, 451 mmol) in 1000 mL of ethanol was added 10 mL of sulfuric acid. The mixture was refluxed over night, cooled down and was neutralized by adding calcium hydroxide in small portions (˜30 g). The suspension was filtered over celite and concentrated in vacuo. The crude product was purified by vacuum distillation yielding 76.4 g (95%) of 1 as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 1.38 (t, J=7.3 Hz, 3H), 2.34 (s, 3H), 2.57 (s, 3H), 4.33 (q, J=7.2 Hz, 2H), 7.01-7.06 (m, 2H), 7.82 (d, J=8.5 Hz, 1H); 13C-NMR (100 MHz, CDCl3): δ 14.3, 21.3, 21.7, 60.4, 126.3, 126.9, 130.7, 132.4, 140.1, 142.3, 167.6; MS (ESI) m/z=133.0 (100), 132.0 (57), 178.1 (M+, 51).

Source