Isolation of high-purity friedelin and 3-hydroxyfriedel-3-en-2-one from cork smoker wash solids

Cork smoker wash solids (black wax) that is obtained in the process of making corkboard by treating ground cork with superheated steam useless waste, generating environmental problems. On other hand, black wax a rich source friedelin (1) and 3-hydroxyfriedel-3-en-2-one (3), pentacyclic triterpenoids belonging to friedelane family. In present work, simple, fast, efficient procedure for extraction highly purified from presented. Extraction hexane or acetone afforded mixture 3-hydroxyfriedel-3-en-2-one. However, chromatographic separation 1 3, due their very similar Rf coefficients, difficult, especially on multigram scale. Therefore, conversion an acetyl derivative 4 was proposed acetylation above mixture. Appropriate selection eluent sequence allows rapid resulting 4.