Reacción #81554

Ecuación de reacción

4-mercaptobenzoic acid

sulfuric acid

methyl alcohol

→

title product

Methyl 4-mercaptobenzoate

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is then warmed
2. 2
   Temperaturato reflux for 16 h
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   workup.ADDITIONdiluted with ethyl acetate (100 mL)
5. 5
   Lavadowashed with saturated sodium bicarbonate (2×100 mL)
6. 6
   OtroThe organic phase is then separated
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 4-mercaptobenzoic acid (Apin, 1.72 g, 11.17 mmol) in anhydrous methyl alcohol (20.0 mL) was added concentrated sulfuric acid (0.43 mL). The reaction mixture is then warmed to reflux for 16 h, concentrated in vacuo, diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (2×100 mL). The organic phase is then separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 712 mg (Y: 38%) of the title product; 1H-NMR (CDCl3): δ7.89 (d, J=8.7 Hz, 2H), 7.29 (d, J=8.7 Hz, 2H), 3.90 (s, 3H), 3.60 (s, 1H).

Fuente