Methanol → Methyl 4-(hydroxymethyl)-6-methylpicolinate

Participants

Reaction Conditions

Reaction Steps

A mixture of 440 mg of the 4-(hydroxymethyl)-6-methylpicolinonitrile in 3 mL of concentrated H2SO4 and 1.8 mL of H2O was stirred at 135° C. for 12 h. The temperature was decreased to 95° C., 6 mL of MeOH was added, and the solution was stirred at 95° C. for 1 h. The solution was added to ice with H2O and EtOAc. Solid NaHCO3 and sat. NaHCO3 solution were added to a pH=8. The aqueous layer was extracted with EtOAc (2×). The combined extracts washed with brine (40 mL), dried over Na2SO4, filtered and concentrated to give 393 mg of methyl 4-(hydroxymethyl)-6-methylpicolinate which was used without further purification.

Provenance & Evidence