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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
3-Acet-oxy-2-naphthoic acid
Abstract:
In the title compound, C(13)H(10)O(4), an analog of acetyl-salicylic acid, the naphthalene unit is twisted slightly due to ortho disubstitution [dihedral angle between conjugated rings system in the naphthalene unit = 2.0 (2)°]. The mean planes of the carb-oxy-lic and ester groups are almost coplanar and perpendicular, respectively, to the mean plane of the conjugated aromatic system, making dihedral angles of 8.9 (3) and 89.3 (1)°. In the crystal, mol-ecules are paired through their carb-oxy-lic groups by the typical centrosymmetric O-H⋯O inter-actions with R(2) (2)(8) hydrogen-bond motifs. In addition, several weak C-H⋯O inter-molecular contacts are also observed. Finally, the mol-ecules are stacked along crystallographic [100] and [010] directions.
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The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
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Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...