Benzene → HCID 20243240, compound

Participants

Reaction Steps

2-Isocaproyl-4-(3-methylbuten-2-yl)phloroglucinol (7) (2 g) was suspended in benzene (25 ml), Trifluoro acetic acid (1.5 ml) was added and the mixture was stirred for 6 hours at room temperature. The resulting solution was stripped to dryness under vacuum. The residue was chromatographed, preferably on silica gel (open column chromatography, preparative HPLC or preparative TLC) using preferably mixtures of benzene and ethyl acetate or petroleum ether and ethyl acetate for eluation. Two chromanes, namely 5,7-dihydroxy-2,2-dimethyl-8-isocaproyl chroman (31) and 5,7-dihydroxy-2,2-dimethyl-6-isocaproyl chroman (33), were obtained in a ratio of about 3 to 2. These chromanes were both recrystallized from petroleum ether to give light straw coloured crystals.

Provenance & Evidence