2004
DOI: 10.3390/90400256
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Preparation of New 2,3-Diphenylpropenoic Acid Esters – Good Yields Even for the More Hindered Z Isomers

Abstract: Abstract:The potassium salt of E-and Z-2,3-diphenylpropenoic acids prepared in situ could be esterified efficiently in DMSO with the appropriate alkyl halides at room temperature. In this way 10 previously undescribed esters of these acids were synthesised and characterised. Excellent yields were observed for most of the E isomers and the more hindered Z esters were also obtained in good yields, far better than those obtained applying the classical acid-catalysed esterification reaction.

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Cited by 4 publications
(3 citation statements)
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“…We report herein a general method for the synthesis of methylcinnamate derivatives of 15‐crown‐5 from the respective chromenone‐crown ethers. The phenylacrylic acids have been prepared by a synthesis from the corresponding chromenone‐crown ethers with MeONa solution in MeOH refluxed for 4 h to afford 5a [11–13] or KOH and DMSO as solvent at 60°C for 3–6 h. The phenolic hydroxyl group was methylated with CH 3 I to give desired compounds 5b , 5c , 5d , 5e , 5f , 5g in quantitative yield [14, 15]. The structures of all synthesized compounds were identified by elemental analysis, IR, 1 H NMR, and mass spectrometry.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…We report herein a general method for the synthesis of methylcinnamate derivatives of 15‐crown‐5 from the respective chromenone‐crown ethers. The phenylacrylic acids have been prepared by a synthesis from the corresponding chromenone‐crown ethers with MeONa solution in MeOH refluxed for 4 h to afford 5a [11–13] or KOH and DMSO as solvent at 60°C for 3–6 h. The phenolic hydroxyl group was methylated with CH 3 I to give desired compounds 5b , 5c , 5d , 5e , 5f , 5g in quantitative yield [14, 15]. The structures of all synthesized compounds were identified by elemental analysis, IR, 1 H NMR, and mass spectrometry.…”
Section: Resultsmentioning
confidence: 99%
“…The resulting mixture was poured into 30–50 mL icy water. The precipitate was collected by filtration, washed with water, and dried to give product 5b , 5c , 5d , 5e , 5f , 5g [14, 15].…”
Section: Methodsmentioning
confidence: 99%
“…1, 136.0, 132.6, 128.3, 125.8, 124.3, 124.2, 122.8, 122.7, 68.9, 21.8;IR (KBr): 2921, 2854, 1713, 1270, 1103 Isopropyl (E)-2,3-Diphenylacrylate (3m). 21 26.0 mg, 50% yield, colorless oil; R f = 0.2 (petroleum ether); 1 H NMR (500 MHz, CDCl 3 ) δ: 7.79 (s, 1H), 7.32−7.34 (m, 3H), 7.12−7.22 (m, 5H), 7.03−7.05 (m, 2H), 5.10−5.17 (m, 1H), 1.27 (d, J = 6.5 Hz, 6H); 13 C{ 1 H} NMR (126 MHz, CDCl 3 ) δ: 167. 3, 139.9, 136.0, 134.8, 133.3, 130.5, 129.9, 128.8, 128.5, 128.2, 127.7, 68.6, 21.9; IR (KBr): 2975, 1702, 1247, 1100, 756 cm −1 ; HRMS (APCI, m/z): + H, 267.1380; found, 267.1372.…”
Section: ■ Conclusionmentioning
confidence: 99%