Methyl 3-methoxy-2-methylbenzoate → (3-Methoxy-2-methylphenyl)methanol

Participants

Reaction Steps

A suspension of 4.5 g (0.118 mol) of lithium aluminum hydride in 100 mL of THF was treated dropwise with a solution of 14.22 g (78.9 mmol) of methyl 3-methoxy-2-methylbenzoate in 120 mL of THF. The mixture was heated at reflux for 2.5 hours, then cautiously decomposed with 1NH2SO4. The mixture was extracted with EtOAc, and the EtOAc washed with dilute HCl, H2O, saturated NaHCO3, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 11.5 g (95.8% yield) of the product as a tan solid, mp 63-64° C. The structure was confirmed by NMR and mass spectroscopy MS n/z 153 (M+H+).

Provenance & Evidence