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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
tert-Butyl 2-methyl-2-(4-nitro-benzo-yl)propanoate
Chelsey M Crosse1, Marshall W Logue, Rudy L Luck
1Department of Chemistry, 1400 Townsend Drive, Michigan Technological University, Houghton, MI 49931, USA.
Abstract:
The title compound, C(15)H(19)NO(5), is bent with a dihedral angle of 61.8 (2)° between the mean planes of the benzene ring and a group encompassing the ester functionality (O=C-O-C). The dihedral angle of 0.8 (2)° between the mean planes of the nitro group and the benzene ring indicates near coplanarity. In the crystal, each mol-ecule is linked to four adjacent mol-ecules by weak C-H⋯O hydrogen-bonding inter-actions. Both benzene H atoms ortho to the ketone O atom form C-H⋯O hydrogen bonds with the keto O atoms of two neighboring mol-ecules (of the keto and ester groups, respectively), and the two other inter-actions involve the H atoms from a methyl group of the dimethyl residue, displaying C-H⋯O inter-actions with the O atoms of the nitro groups. These four inter-actions for each mol-ecule lead to the formation of two-dimensional sheets with a hydro-philic inter-ior, held together by weak hydrogen-bonded inter-actions, and a hydro-phobic exterior composed of protruding methyl groups which interst-ack with the methyl groups in adjacent sheets.
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