Synthetic Route of 504-63-2 ,Some common heterocyclic compound, 504-63-2, molecular formula is C3H8O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
General procedure A: Synthesis of acetal protected aldehydes 1,3-Propanediol (1.5 eq.) and p-TSA (0.1 eq.) were added to a solution of aldehyde (5.0 mmol, 1.0 eq.) in toluene. The reaction was heated to reflux and left to stir for 7 hours. After cooling to room temperature, the reaction was washed with three portions of H2O, dried over MgSO4 and the solvent removed under reduced pressure to afford the crude acetal protected product. General procedure A was followed using 2-bromobenzaldehyde (925 mg, 5.00 mmol), followed by recrystallization from petrol:ether, to provide the title compound as white needles in 88% yield (1.07g, 4.40 mmol). m.p. 83-84 C; 1H NMR (300 MHz, CDCl3) deltaH: 7.69 (1H, dd, J = 7.8, 1.7 Hz, ArH), 7.52 (1H, dd, J = 8.0, 1.3 Hz, ArH), 7.33 (1H, td, J = 7.6, 1.2 Hz, ArH), 7.19 (1H, td, J = 7.7, 1.7 Hz, ArH), 5.76 (1H, s, CH), 4.29 (1H, dd, J = 5.1, 1.3 Hz, OCHAHB), 4.25 (1H, dd, J = 5.1, 1.3 Hz, OCHAHB), 4.03 (2H, td, J = 12.2, 2.4 Hz, OCH2), 2.32-2.16 (1H, m, CH2CHAHBCH2), 1.48-1.41 (1H,m, CH2CHAHBCH2); 13C{1H} NMR (75.5 MHz CDCl3) deltaC: 137.5, 132.6, 130.3, 128.0, 127.5, 122.3, 100.9, 67.6, 25.7; I.R (thinfilm) nu max (cm-1): 1594 (ArC=C), 1570 (ArC=C); HRMS (ESI): m/z calculated for C10H11BrO2: requires: 264.9840 for [M+Na]+; found: 264.9839.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,504-63-2, its application will become more common.
Reference:
Article; Peacock, Lucy R.; Chapman, Robert S. L.; Sedgwick, Adam C.; Bull, Steven D.; Mahon, Mary F.; Amans, Dominique; Organic Letters; vol. 17; 4; (2015); p. 994 – 997;,
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