1,5-Dihydroxynaphthalene → HCID 14814248, compound

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Reaction Steps

12 g (0.3 Mol) sodium hydroxide are dissolved while heating in 500 ml ethanol and a solution of 25 g (0.15 Mol) 1,5-dihydroxynaphthalene 97% is added to the cooled solution within 20 minutes. Afterwards 40.23 g (0.15 Mol) n-decyl iodide is added dropwise within 20 minutes and it is subsequently boiled for 4 hours under reflux. After aspiration of the inorganic residue, the filtrate is concentrated in a vacuum and the dark-brown, semi-crystalline residue is purified by column chromatography on silica gel 60 (Merck). Mobile solvent: toluol/methanol=7:1. After recrystallization from n-heptane the corresponding eluate yields 11.5 g (25.3% of the theroretical yield) product, light-brown crystals, Fp 85°-87° C.

Provenance & Evidence