Preparation of cis-4-tert-butyl-cis-3-hydroxycyclohexaneacetonitrile (2) and the parent cis-3- hydroxycyclohexaneacetonitrile (1) is described. In intermediates leading to 2 severe crowding at axially substituted C (3) leads to unusual reactions, including rapid intramolecular oxonium ion formation at 0-5 OC, abnormally easy hydride reduction of a nitrile, and formation of an open-chain hemiacetal that is relatively stable to aqueous acid.
