p-Toluenesulfonic acid → HCID 18979162, compound

Participants

Reaction Steps

1,4-Naphthohydroquinone (8 g) was reacted with 6-hydroxy-6-(4-methoxyphenyl)hexanoic acid (11.9 g) in the presence of p-toluenesulfonic acid (3.8 g) in toluene (200 ml) at 80° C. for 15 hours. Then, the reaction mixture was extracted with ethyl acetate and concentrated. The residue was submitted to an overnight reaction with an aqueous solution (120 ml) of iron (III) chloride hexahydrate (31 g) (0.1 ml) in acetic acid (70 ml) at room temperature. This reaction mixture was extracted with ethyl acetate and concentrated and the residue was purified by silica gel column chromatography. Recrystallization from hexane-ethyl acetate gave 4 g of the title compound.

Provenance & Evidence