(2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile) synthesis
- Product Name:(2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile)
- CAS Number:27334-24-3
- Molecular formula:C19H18N2O
- Molecular Weight:290.36
23051-44-7
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Yield:27334-24-3 89%
Reaction Conditions:
with piperidine in ethanol;Reflux;
Steps:
Compound 2
Equimolar amounts of 4-hydrox-benzaldehyde and appropriate active 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile were heated in a small volume of ethanol under reflux in the presence of a few drops of piperidine catalyst. When the reaction was judged complete by thin layer chromatography, the solvent was evaporated under reduced pressure and the product purified by recrystallization from ethanol, or by column chromatography (silica/dichloromethane), Yield 89%. 1H NMR (600 MHz, 25°C, DMSO-d6): δ 9.98 (s, 1H), 7.55 (d, 2H) 7.22 (d, 2H), 6.80 (t, 3H), 2.60 (d, 2H), 2.53 (d, 2H), 1.01 (m, 6H); 13C NMR (150 MHz, DMSO-d6): δ 169.9, 159.0, 156.4, 138.0, 129.6, 126.8, 126.0, 121.1, 115.6, 113.8, 113.0, 74.5, 42.0, 40.1, 38.4, 37.9, 31.4, 27.1; calcd. for C19H18N2O [M+1]+: 291.14, found 291.15 (Fig.S2).
References:
Huo, Fangjun;Zhang, Yaqiong;Yue, Yongkang;Chao, Jianbin;Zhang, Yongbin;Yin, Caixia [Dyes and Pigments,2017,vol. 143,p. 270 - 275]
78-59-1
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