4,4’-(1,3-Propanediyl)dioxydibenzaldhyde synthesis
- Product Name:4,4’-(1,3-Propanediyl)dioxydibenzaldhyde
- CAS Number:3722-80-3
- Molecular formula:C17H16O4
- Molecular Weight:284.31
123-08-0
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Yield:3722-80-3 92%
Reaction Conditions:
Stage #1: 4-hydroxy-benzaldehydewith potassium carbonate in water;acetone at 20; for 0.166667 h;
Stage #2: 1,3-dibromo-propane in water;acetone at 20; for 4 h;
Steps:
General Procedure for the Synthesis of Substituted 1,3-bis(4-carboxaldehydephenoxy)propane (13, 14)
The 4-hydroxybenzaldehyde or vanillin (1 eq) was dissolved in acetone. Potassium carbonate (4.5 eq) dissolved in water was added dropwise and stirred for 10 minutes at room temperature. 1,3-dibromopentane (0.5 eq) dissolved in acetone was added dropwise. Stirring was continued for 4 h. After completion of reaction, determined by thin layer chromatography,the solvent was evaporated under vacuum to afford crude product, which was washed with water, filtered and recrystallized from ethanol-water mixture. 4,4'-[propane-1,3-diylbis(oxy)]dibenzaldehyde (13):Yield: 92%, mp: 179.6 - 180.5 °C. 1H-NMR (DMSO-d6, 200MHz, Me4Si) (ppm): 2.21 (t, 2H, -CH2- propylene bridge),4.22 (s, 4H, -O-CH2-), 7.10 (d, 8.6, 4H, aromatic proton, H-3, H-5), 7.82 (d, 8.6, 4H, aromatic proton H-2, H-6), 9.82 (s,2H -CHO). 13C-RMN (50 MHz, DMSO-d6, Me4Si): 28.7 (C-2’), 85.2 (C-1’), 115.3 (C-3, C-5), 130.1 (C-4), 132.2 (C-2,C-6), 163.8 (C-1), 191.6 (-CHO). MS/FAB+: m/z 285(M+H+). (Calcd for C17H16O4H+ 285.31)
References:
Méndez-Cuesta, Carlos A.;Herrera-Rueda, Miguel ángel;Hidalgo-Figueroa, Sergio;Tlahuext, Hugo;Moo-Puc, Rosa;Chale-Dzul, Juan Bautista;Chan-Bacab, Manuel;Ortega-Morales, Benjamín Otto;Hernández-Nú?ez, Emanuel;Méndez-Lucio, Oscar;Medina-Franco, José L.;NavarreteVázquez, Gabriel [Medicinal Chemistry,2016,vol. 12,p. 1 - 12]
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40663-68-1
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3722-80-3
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17954-81-3
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632-02-0
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3722-80-3
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82625-25-0
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142-28-9
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3722-80-3
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