ChemicalBook CAS DataBase List 4,4’-(1,3-Propanediyl)dioxydibenzaldhyde

4,4’-(1,3-Propanediyl)dioxydibenzaldhyde synthesis

7synthesis methods

Product Name:4,4’-(1,3-Propanediyl)dioxydibenzaldhyde
CAS Number:3722-80-3
Molecular formula:C17H16O4
Molecular Weight:284.31

123-08-0

109-64-8

4,4’-(1,3-Propanediyl)dioxydibenzaldhyde

3722-80-3

General procedure: 4-Hydroxybenzaldehyde (1 eq.) is dissolved in acetone. Potassium carbonate (4.5 eq.) dissolved in water was added slowly and the reaction mixture was stirred at room temperature for 10 minutes. Subsequently, 1,3-dibromopropane (0.5 eq.) dissolved in acetone was added dropwise. The reaction mixture was continued to be stirred for 4 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was washed with water, filtered and recrystallized from ethanol-water mixed solvent to give 4,4'-(propane-1,3-diylbis(oxy))dibenzaldehyde (13). Yield: 92%, melting point: 179.6-180.5 °C. 1H-NMR (DMSO-d6, 200 MHz, Me4Si) δ (ppm): 2.21 (t, 2H, -CH2-propylidene-bridged), 4.22 (s, 4H, -O-CH2-), 7.10 (d, J = 8.6 Hz, 4H, aryl proton, H-3, H-5), 7.82 (d, J = 8.6 Hz, 4H, aromatic proton, H-2, H-6), 9.82 (s, 2H, -CHO).13C-NMR (50 MHz, DMSO-d6, Me4Si) δ: 28.7 (C-2'), 85.2 (C-1'), 115.3 (C-3, C-5), 130.1 (C-4), 132.2 (C-2, C-5), 132.2 (C-4), 132.2 (C-4), 132.2 (C-4), 132.2 (C-4), 132.2 (C-4), 132.2 (C-4), 132.2 (C-4) 132.2 (C-2, C-6), 163.8 (C-1), 191.6 (-CHO).MS/FAB+: m/z 285 (M + H+). (calculated value C17H16O4H+ 285.31).

123-08-0 Synthesis

123-08-0
953 suppliers
$5.00/10g

109-64-8 Synthesis

109-64-8
506 suppliers
$10.00/5g

3722-80-3
27 suppliers
$20.00/100mg

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]

123-08-0 Synthesis

123-08-0
953 suppliers
$5.00/10g

109-64-8 Synthesis

109-64-8
506 suppliers
$10.00/5g