Abstract o-Iodocardanol, readily available from cardanol by iodination, has been used to prepare a variety of lipophilic benzo [b] furans. 2-Substituted benzo [b] furans have been prepared by a Sonogashira cross-coupling/cyclization process. 2, 3-Disubstituted benzo [b] furans have been obtained from o-alkynylcardanols by an oxypalladation/reductive elimination process.