Phenol → HCID 14937588, compound

Participants

Reaction Steps

To a solution of AlCl3 (1.42 g) in dichloromethane (20 mL) at 0° C. is added a solution of phenol (1 g) in dichloromethane (20 mL) and the mixture is stirred at this temperature for 40 minutes. After addition of a solution of pyridine-2-carboxaldehyde (1.21 g) in dichloromethane (10 mL), the mixture is allowed to warm at room temperature for 4 hours, then cooled to 0° C., treated dropwise with aqueous ammonium chloride and stirred at room temperature for 30 minutes. The aqueous phase is extracted twice with dichloromethane and pooled organic extracts dried over magnesium sulfate and concentrated. The residue is purified by column chromatography over silica gel (gradient heptane/ethyl acetate from 100/0 to 70/30) to afford pure 2-(hydroxy-pyridin-2-yl-methyl)-phenol.

Provenance & Evidence