Synthesis, crystal structure and spectral characterization
of 5-methyl-2-(propan-2-yl)cyclohexyl cyanoacetate
and
1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl cyanoacetate
- Received: August, 28, 2024
- Revised: November, 9, 2024
- Accepted for publication: November, 9, 2024
- DOI 10.26902/JSC_id140800
- EDN: ZCJUNX
- Views: 159
1 Chemistry Department, Faculty of Science, Ain Shams University, Cairo, Egypt
2 Faculty of Chemistry, Wrocław University of Science and Technology, Wrocław, Poland
3 Green Chemistry Department, National Research Centre, Cairo, Egypt
The titled compounds were synthesized using a conventional esterification method, involving the reaction of the desired alcohol with cyanoacetic acid. Single crystal was obtained through recrystallization. The compounds were characterized using elemental analysis, IR, 1H NMR, 13C NMR
spectroscopy, and mass spectrometry. The structural parameters, including bond
distances and angles, were analyzed and discussed based on X-ray study result.
The study revealed that the hydrogen atoms of the methylene groups in the two
synthesized compounds exhibit a rigid C—H rotating group. The absolute
configuration of the stereogenic centers in both compounds was consistent with
the substrate used in their synthesis.
Keywords: cyanoacetylation, menthol, fenchol, menthyl cyanoacetate, fenchyl cyanoacetate, crystal structure, X-ray study
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