Reacción #1605771

Ecuación de reacción

2-hydroxy-4-methylbenzoic acid

K2CO3

KOH

HCl

→

2-methoxy-4-methylbenzoic acid

Disolventes

acetone

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture heated
2. 2
   Temperaturaat reflux for 48 hrs
3. 3
   Filtraciónwas filtered
4. 4
   Otrothe filtrate was evaporated
5. 5
   Otroto give the crude methyl 2-methoxy-4-methylbenzoate
6. 6
   Temperaturathe solution heated
7. 7
   Temperaturaat reflux 48 hrs
8. 8
   TemperaturaAfter cooling the reaction mixture
9. 9
   Extracciónextracted with ethyl acteate
10. 10
    LavadoThe organic layer was washed with brine
11. 11
    Secadodried over MgSO4
12. 12
    Filtraciónfiltered
13. 13
    Otroevaporated
14. 14
    OtroThe residue was triturated with Ethyl acetate/Hexane

Procedimiento

To a solution of 2-hydroxy-4-methylbenzoic acid (25 g, 0.164 mol) in acetone (350 mL) was added K2CO3 (68 g, 0.492 mmol) followed by MeI (41 mL, 0.656 mmol) and the reaction mixture heated at reflux for 48 hrs. After cooling to r.t. the reaction mixture was filtered and the filtrate was evaporated to give the crude methyl 2-methoxy-4-methylbenzoate. KOH (11.3 g, 1.2 eq) was dissolved in MeOH (300 mL) and the crude ester was added to the mixture and the solution heated at reflux 48 hrs. After cooling the reaction mixture was acidified with aq. HCl (1N) and extracted with ethyl acteate. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was triturated with Ethyl acetate/Hexane to give 20 g of 2-methoxy-4-methylbenzoic acid as a cream white solid (85% yield)

Fuente