In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 56-81-5 as follows., 56-81-5
4.2.7 cis-2-Phenyl-1,3-dioxan-5-ol (18) Concentrated sulfuric acid (3 drops) was added to a mixture of glycerol (44 mL, 55 g, 0.60 mol) and freshly distilled benzaldehyde (48 mL, 50 g, 0.47 mol) in toluene (69 mL). The resulting mixture was heated to reflux in a Dean-Stark water separator. When the separation of water was complete (8.5 mL), the reaction mixture was allowed to cool to room temperature and the solvent removed in vacuo. The resulting white solid was recrystallized from isopropyl ether/petroleum ether. The precipitate was filtered off and purified by flash column chromatography (? = 6 cm, h = 15 cm, V = 50 mL, cyclohexane/ethyl acetate = 2:1, Rf = 0.16) to give 18 as colorless solid (42.6 g, 0.24 mol, 50% yield). Mp = 81 C; 1H NMR (DMSO-d6): delta [ppm] = 3.48-3.52 (m, 1H, OCH2CHOH), 3.91-3.97 (m, 2H, OCH2CHOH), 4.01-4.07 (m, 2H, OCH2CHOH), 4.99 (d, J = 4.8 Hz, 1H, OH), 5.53 (s, 1H, CHPh), 7.33-7.40 (m, 3H, 3′-Hphenyl, 4′-Hphenyl, 5′-Hphenyl), 7.42-7.47 (m, 2H, 2′-Hphenyl, 6′-Hphenyl); 13C NMR (DMSO-d6): delta [ppm] = 62.4 (1C, OCH2CHOH), 71.4 (2C, OCH2CHOH), 100.2 (1C, CHPh), 126.2 (2C, C-2’phenyl, C-6’phenyl), 127.9 (2C, C-3’phenyl, C-5’phenyl), 128.5 (1C, C-4’phenyl), 138.9 (1C, C-1’phenyl); IR (neat): [cm-1] = 3271, 2916, 2851, 1450, 1385, 1339, 1277, 1153, 1084, 995, 976, 806, 741, 694; HRMS (m/z): [M+H]+ calcd for C10H13O3, 181.0859; found, 181.0878; HPLC (method 1): tR = 11.7 min, purity 95.4%.
The chemical industry reduces the impact on the environment during synthesis 56-81-5, I believe this compound will play a more active role in future production and life.
Reference:
Article; Tangherlini, Giovanni; Torregrossa, Tullio; Agoglitta, Oriana; Koehler, Jens; Melesina, Jelena; Sippl, Wolfgang; Holl, Ralph; Bioorganic and Medicinal Chemistry; vol. 24; 5; (2016); p. 1032 – 1044;,
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