Synthesis method of polyaryl substituted aldehyde compound
An aldehyde compound and a synthesis method technology are applied in the field of synthesis of polyaryl-substituted aldehyde compounds, can solve problems such as toxic hydrogen bromide by-products, do not conform to green chemistry, etc., and achieve high catalyst efficiency, good industrial production prospects, and high productivity. high rate effect
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[0020] A kind of synthetic method of polyaryl substituted aldehydes compound in the present application comprises the steps: (1) prepare reaction substrate: diaryl carbinol compound and aryl-1,2-ethanediol compound, add Catalyst: polymetallic oxygen cluster compound, under organic solvent condition, carries out reaction (reaction schematic diagram is as image 3 );
[0021] (2) After the reaction is completed, the product polyaryl-substituted aldehydes are obtained.
[0022] Aiming at the problems of low yield, many by-products and expensive catalysts in the existing methods, the present invention uses a cheap, efficient and green catalyst—Keggin type polymetallic oxygen clusters to catalyze the synthesis of diphenylcarbinol compounds and phenylacetaldehyde compounds The multi-substituted aryl aldehyde compound uses a highly efficient, green, cheap catalyst, mild reaction conditions, high yield, and the only by-product is water. The reaction adopts the "one-pot cooking" meth...
Embodiment 1
[0032] Weigh 0.2mmol benzylmethanol, 0.24mmol 1-phenyl-1,2-ethanediol and 3mol% H 3 PW12 o 40 The catalyst was placed in a 4mL reaction bottle, 1mL of nitromethane solvent was added, and a stirring magnet was added, then sealed, and reacted at 90°C for 2 hours. After the reaction, the target product was obtained by column chromatography separation with a yield of 87%.
[0033] The specific results are as follows:
[0034]
[0035] 1 HNMR (400MHz, CDCl 3 ): δ(ppm)9.69(s,1H),7.37-7.39(m,2H),7.30(t,J=14.4,7.2Hz,2H),7.08-7.24(m,10H),6.99-7.02(m ,1H),4.77(d,J=12Hz,1H),4.51(d,J=12Hz,1H); 13 C NMR (100.6MHz, CDCl 3 ): δ (ppm) 198.85, 142.13, 141.51, 134.41, 129.44, 128.91, 128.89, 128.35, 128.28, 128.13, 127.62, 126.91, 126.34, 63.38, 52.09.
Embodiment 2
[0037] Weigh 0.2mmol 1-phenyl-1-(4-chlorophenyl)methanol, 0.24mmol 1-phenyl-1,2-ethanediol and 3mol% H 3 PW 12 o 40 The catalyst was placed in a 4mL reaction bottle, 1mL of nitromethane solvent was added, and a stirring magnet was added, then sealed, and reacted at 90°C for 2 hours. After the reaction, the target product was obtained by column chromatography separation with a yield of 89%.
[0038] The specific results are as follows:
[0039]
[0040] 1 H NMR (400MHz, CDCl 3 ):δ(ppm)9.68(s,1H),7.28-7.35(m,4H),7.17-7.25(m,6H),7.04-7.10(m,3H),6.99-7.01(m,1H),4.75 (d,J=12Hz,1H),4.47(d,J=12Hz,1H); 13 C NMR (100.6MHz, CDCl 3 ): δ (ppm) 198.44, 141.06, 140.88, 133.92, 132.66, 129.48, 129.45, 129.00, 128.47, 128.22, 127.77, 126.56, 63.40, 51.37.
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