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Updated: Jun 5, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
(±)-trans-3-Benzoyl-bicyclo-[2.2.2]octane-2-carboxylic acid
Roger A Lalancette1, Hugh W Thompson, Andrew P J Brunskill
1Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102, USA.
Abstract:
The title keto acid, C(16)H(18)O(3), displays significant twisting of all three ethyl-ene bridges in its bicyclo-[2.2.2]octane structure owing to steric inter-actions; the bridgehead-to-bridgehead torsion angles are 13.14 (12), 13.14 (13) and 9.37 (13)°. The compound crystallizes as centrosymmetric carboxyl dimers [O⋯O = 2.6513 (12) Å and O-H⋯O = 178°], which have two orientations within the cell and contain no significant carboxyl disorder.
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