2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol
Introduction '''2,2,4,4-Tetramethyl-3-''t''-butyl-pentane-3-ol''' or '''tri''-tert-''butylcarbinol''' is an organic compound with formula C13H28O, ((H3C)3C)3COH, or tBu3COH. It is an alcohol that can be viewed as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-''t''-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH.Tri-''tert''-butylcarbinol is arguably the most sterically hindered alcohol that has been prepared to date. In contrast to all other known alcohols, the infrared spectrum of the liquid does not exhibit a broad OH absorption associated with intermolecular hydrogen bonding, making it interesting for research in spectroscopy. The bulky ''tert''-butyl groups (H3C)3C- groups attached to the central carbon prevent the formation of a O–H---O hydrogen bond with another molecule, an intermolecular interaction typical of alcohols.Another structural analog, in which the COH group is replaced by N, is tri''-tert''-butylamine, a molecule predicted to be stable but has never been prepared.Tri-''tert''-butylcarbinol was first prepared in poor yield using Barbier-type conditions by coupling hexamethylacetone with ''t''-butyl chloride in the presence of sodium sand (5.1 to 8.5% yield), presumably via the organosodium species. Later on, it was shown that under carefully selected conditions, the compound could be prepared in high yield (81%) by addition of ''tert''-butyllithium to hexamethylacetone.
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