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

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2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol
Names
Preferred IUPAC name
3-tert-Butyl-2,2,4,4-tetramethylpentan-3-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H28O/c1-10(2,3)13(14,11(4,5)6)12(7,8)9/h14H,1-9H3 checkY
    Key: LIUBOLYWYDGCSJ-UHFFFAOYSA-N checkY
  • InChI=1/C13H28O/c1-10(2,3)13(14,11(4,5)6)12(7,8)9/h14H,1-9H3
    Key: LIUBOLYWYDGCSJ-UHFFFAOYAS
  • OC(C(C)(C)C)(C(C)(C)C)C(C)(C)C
Properties
C13H28O
Molar mass 200.366 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[1] 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as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-t-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH.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.[2] 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.[3] 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.[4]

References

[edit]
  1. ^ Z. Malarski (1974). "Solid rotator phases in 2,2,4,4-tetramethyl-3-tert-butyl-3-pentanol (t-Bu3COH)". Mol. Cryst. Liq. Cryst. 25 (3–4): 259–272. doi:10.1080/15421407408082805.
  2. ^ 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. Bibcode:2006JMoSt.788...93M. doi:10.1016/j.molstruc.2005.11.022.
  3. ^ Bartlett, Paul D.; Schneider, Abraham (1945). "The Synthesis of Tri-t-butylcarbinol and Other Highly Branched Alcohols by Means of Sodium". Journal of the American Chemical Society. 67 (1): 141–144. doi:10.1021/ja01217a049. ISSN 0002-7863.
  4. ^ Bartlett, Paul D.; Lefferts, Edwin B. (1955). "Highly Branched Molecules. III. The Preparation of Tri-t-butylcarbinol by Means of t-Butyllithium". Journal of the American Chemical Society. 77 (10): 2804–2805. doi:10.1021/ja01615a040. ISSN 0002-7863.
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