Synthesis
General procedure for the synthesis of compounds (CAS:57295-30-4) from 5-(hydroxymethyl)-2-methylphenol: The product of step (i) (440.0 mg, 3.18 mmol) was dissolved in THF (4.4 mL) at room temperature, followed by addition of MnO2 (552.9 mg, 6.36 mmol). The reaction mixture was stirred at 50 °C for 6 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove solid impurities. The filtrate was concentrated and the residue was purified by fast column chromatography to afford the target compound (CAS:57295-30-4) (46.1 mg, 11% yield) as a light yellow solid.1H NMR (CDCl3) δ: 9.90 (1H, s), 7.36 (1H, dd, J = 7.76, 1.44 Hz), 7.30 (1H, s ), 7.29 (1H, d, J = 5.52 Hz), 5.33 (1H, s), 2.33 (3H, s).
Purification Methods
Crystallise it from water or *C6H6 (m 71-71o). The O-methyl ether has m 45-46o (from Et2O/hexane). [Sedgwick & Allott J Chem Soc 2820 1923, Flitsch et al. Justus Liebigs Ann Chem 1413 1985, Beilstein 8 H 100, 8 II 103, 8 IV 368.]
