3-Methylcatechol → 5-tert-Butyl-3-methylpyrocatechol

Participants

Reaction Conditions

Reaction Steps

A 1000 mL three neck flask equipped with stirrer, condenser and thermometer is charged with 3-methylcatechol (25.0 g, 0.20 mole), tert-butanol (38.0 mL, 0.40 mole) and 500 mL of heptane; followed by addition of sulfuric acid (98%, 20 g) slowly. The mixture is heated to 80° C. for 6 hrs until gas chromatography (GC) indicates the completion of the reaction. The solvent is removed in vacuo, and the residue is dissolved in CH2Cl2 and washed with water, NaHCO3 (aq.), brine and dried (Na2SO4). Filtration and concentration yield 5-tert-butyl-3-methylcatechol (36 g, 84%). 1H NMR: 6.79 (s, 1H), 6.75 (s, 1H), 5.01 (br, 1H), 2.29 (s, 3H), 1.29 (s, 9H).

Provenance & Evidence