Related Products of 1579-40-4,Some common heterocyclic compound, 1579-40-4, name is Di-p-tolyl Ether, molecular formula is C14H14O, 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.
A neat mixture of p-tolyl ether (1.784 g, 9.00 mmol), 5-tertbutylisophthalic acid (1.000 g, 4.50 mmol), zinc chloride (4.478 g, 32.86 mmol) and phosphorus oxychloride (3.4 mL, 36 mmol) were heated at 100 C for 24 h under a N2 atmosphere. The mixture was cooled to room temperature to give viscous dark red-orange oil. The tacky reaction product was suspended in EtOAc (150 mL) and loosened with a spatula, before being transferred and quenched with water (250 mL) and rapidly stirred for 0.5 h. The resulting emulsion was extracted with EtOAc (3 100 mL) to give a bright orange solution. The combined organic layers were then washed with water (2 100 mL) to afford a transparent yellow solution, which was dried over Na2SO4, filtered and silica gel added. The solvent was removed by rotary evaporation and the orange silicaabsorbed crude product was purified using flash chromatography on silica gel, eluting with hexanes-EtOAc (9:1). The first colourless fraction was collected, the solvent removed under reduced pressure, yielding 1 as a white solid (1.683 g, 65%). A second slightly pink-tinged band yielded 2 as a pink tinged solid. If CH2Cl2 was used as the extracting solvent, no 2 was obtained and the yield of 1 increased to >85%. Data for 1. M.p. 199e202 C. 1 H NMR (400 MHz, (CD3)2CO): d 7.23 (d, J 1.6, 2H, phen-H), 7.21 (t, J 1.6, 1H, ArH), 7.16 (m, 4H,xan-H), 7.07 (ddd, J 8.3, 2.2, 0.5, 4H, xan-H), 7.00 (d, J 8.3, 4H, xan-H), 5.24 (s, 2H, CeOH), 2.20 (s, 12H, xan-Me), 1.13 (s, 9H, Ar-tBu). 13C{1 H} NMR (100.6 MHz, (CD3)2CO): d 150.50 (Cq), 149.64 (2 Cq), 149.01 (4Cq), 132.96 (4Cq), 130.11 (4ArCeH), 129.51 (4ArCeH), 129.26 (4Cq), 122.74 (1ArCeH), 121.81 (2ArCeH), 116.58 (4ArCeH), 70.99 (2 Cq), 35.36 (t-Bu) 31.75 (3t-Bu), 20.99 (4Ar-Me). IR (ATR): ~nmax=cm1 3746 (vw), 3667 (w), 3642 (w), 3511 (w), 2950 (w), 2916 (w), 2859 (w), 1606 (w), 1482 (s), 1436 (m), 1420 (m), 1359 (m), 1310 (m), 1284 (s), 1257 (s), 1213 (s), 1135 (s), 1110 (m), 1014 (s), 952 (m), 902 (w), 887 (m), 807 (s), 763 (m), 757 (m). ()-HR-ESI-MS: Found m/z 579.2779 (calc. [C41H38O4] : m/z 582.2770).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Di-p-tolyl Ether, its application will become more common.