2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol

changed changed 477209644 2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol 2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol.png 2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol 3D.png 3-tert-Butyl-2,2,4,4-tetramethylpentan-3-ol correct chemspider 125760 1/C13H28O/c1-10(2,3)13(14,11(4,5)6)12(7,8)9/h14H,1-9H3 LIUBOLYWYDGCSJ-UHFFFAOYAS correct chemspider 1S/C13H28O/c1-10(2,3)13(14,11(4,5)6)12(7,8)9/h14H,1-9H3 correct chemspider LIUBOLYWYDGCSJ-UHFFFAOYSA-N correct CAS 41902-42-5 correct FDA 4UH2D93L3U 142558 OC(C(C)(C)C)(C(C)(C)C)C(C)(C)C 13 28 1 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. Z. Malarski Solid rotator phases in 2,2,4,4-tetramethyl-3-tert-butyl-3-pentanol (t-Bu3COH) 1974 Mol. Cryst. Liq. Cryst. 25 3–4 259–272 10.1080/15421407408082805 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as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-t-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH.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. Irena Majerza Ireneusz Natkaniec 2006 Experimental and theoretical IR, R, and INS spectra of 2,2,4,4-tetramethyl-3-t-butyl-pentane-3-ol J. Mol. Struct. 788 1–3 93–101 10.1016/j.molstruc.2005.11.022 2006JMoSt.788...93M 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.Bartlett Paul D. Schneider Abraham 1945 The Synthesis of Tri-t-butylcarbinol and Other Highly Branched Alcohols by Means of Sodium https://pubs.acs.org/doi/abs/10.1021/ja01217a049 Journal of the American Chemical Society en 67 1 141–144 10.1021/ja01217a049 1945JAChS..67..141B 0002-7863 subscription 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.Bartlett Paul D. Lefferts Edwin B. 1955 Highly Branched Molecules. III. The Preparation of Tri-t-butylcarbinol by Means of t-Butyllithium https://pubs.acs.org/doi/abs/10.1021/ja01615a040 Journal of the American Chemical Society en 77 10 2804–2805 10.1021/ja01615a040 1955JAChS..77.2804B 0002-7863 subscription References Category:Tertiary alcohols Category:Tert-butyl compounds Category:Alkanols