Reacción #9038

Ecuación de reacción

dimethyl sulfate

ethyl 6-methylsalicylate

lithium hydroxide monohydrate

→

ethyl 2-methoxy-6-methylbenzoate

Rendimiento 91.0%

Disolventes

diethyl ether

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 1 hour
2. 2
   Lavadowashed with saturated aqueous NaHCO3 (4×10 mL)
3. 3
   Secadodried (MgSO4)
4. 4
   Concentraciónconcentrated
5. 5
   OtroPurification of the crude material by column chromatography on silica gel (9:1 hexanes-EtOAc)

Procedimiento

To a solution of ethyl 6-methylsalicylate (1.27 g, 6.97 mmol) in THF (35 mL) was added lithium hydroxide monohydrate (0.594 g, 14.2 mmol) followed by dimethyl sulfate (1.00 mL, 10.6 mmol). The resultant mixture was heated to reflux for 1 hour then cooled to room temperature. The mixture was diluted with diethyl ether (70 mL), washed with saturated aqueous NaHCO3 (4×10 mL), dried (MgSO4) and concentrated. Purification of the crude material by column chromatography on silica gel (9:1 hexanes-EtOAc) provided 1.23 g (91%) of ethyl 2-methoxy-6-methylbenzoate as a white solid. 1H NMR (CDCl3) δ 1.38 (t, 3H, J=7.2 Hz), 2.30 (s, 3H), 3.82 (s, 3H), 4.40 (q, 2H, J=7.2 Hz), 6.76 (d, 1H, J=8.4 Hz), 6.79 (d, 1H, J=7.8 Hz), 7.23 (dd, 1H, J=7.8, 8.4 Hz).

Fuente