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

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: 92percent, 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)The exemplary process of the invention is shown schematically in Figure 1.0 Step (a): 4-(3-Bromopropyloxy)benzaldehyde (Compound 1)A dry Belatech glass reactor (30L) was flushed with argon and charged with 4- hydroxybenzaldehyde (588g, 4.8MoIe), 1, 3-dibromopropane (4.976kg, 24.6MoIe) and anhydrous acetonitrile (24L) under argon. Dried powdered 5 potassium carbonate (1.66kg, 12MoIe) was added in portions to the stirred solution. The suspension was stirred at 55-60°C and monitored by gas chromatography and cooled (ice bath) to room temperature as soon as the 4- hydroxybenxaldehyde had been consumed (3-4hr). Solids were removed by filtration (2L Buechner funnel) and washed with dry acetonitrile (3 x 300 mL). , 0 The combined solvents were reduced in volume by rotary evaporation (bath temperature 40General procedure: To a mixture of tosylate 8 (45.63 g, 0.183 mol) and powdered K2CO3 (36.26 g, 0.262 mol), 4-hydroxybenzaldehyde (6) (24.95 g, 0.201 mol; R

Molecular Weight:284.31
XLogP3:2.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:8
Exact Mass:284.10485899
Monoisotopic Mass:284.10485899
Topological Polar Surface Area:52.6
Heavy Atom Count:21
Complexity:272
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes