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Updated: Jun 2, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
4,4,4-Trifluoro-3-hy-droxy-3-(trifluoro-meth-yl)butanoic acid
Richard Betz1, Thomas Gerber, Henk Schalekamp
1Nelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.
Abstract:
The asymmetric unit of the title compound, C(5)H(4)F(6)O(3), a polyfluorinated derivative of β-hy-droxy-butyric acid, comprises two mol-ecules. Intra-molecular O-H⋯O hydrogen bonds occur. In the crystal, inter-molecular O-H⋯O hydrogen bonds give rise to the formation of carb-oxy-lic acid dimers. Along with these hydrogen bonds, C-H⋯O contacts connect the mol-ecules into infinite strands along the a axis.
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Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
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.
IUPAC Nomenclature of Carboxylic Acids
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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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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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...
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