The Synthesis and Structure of 3,4-Di-t-butylbenzoic Acid

Abstract

3,4-Di-t-butylbenzoic acid (1) was synthesized by a seven-step sequence from 4-t-butylbenzoic acid, and its structure was determined by X-ray diffraction and refined to a residual of 0.065 for 1403 independent observed reflections. The crystals are triclinic, Pī , a 6.080(1), b 8.777(1), c 13.912(3)Ǻ, α 80.76(2), β 80.84(2), γ 75.62(2)°. It is the only example of a simple ortho-di-t-butylbenzene whose structure has been determined. The benzene ring experiences some out-of-plane distortion but, in general, strain is relieved by in-plane bond stretching and angular distortions.