Orcinol → 7-Hydroxy-2,2,5-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one

Participants

Reaction Steps

Anhydrous 5-methylbenzen-1,3-diol (3.678 g), 3,3-dimethylacrylic acid (3.3 mL) and aluminum chloride (14.76 g) were added to phosphoryl chloride (45 mL) and the mixture was shaken at room temperature for 6 hours. The reaction solution was poured into ice, and the precipitates were filtered, washed with water and dried. The precipitates were purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=25/1) to give the titled compound (3.8 g) as a colorless powder.

Provenance & Evidence