In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol, the common compound, a new synthetic route is introduced below. Application In Synthesis of (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol
Example 1A; 5,5′-Bis(octyloxymethyl)-2-phenyl-1 ,3-dioxane (1 a); 1a[00105] Sodium hydride (60% oil dispersion, washed with hexanes, 8.6 g, 0.22 mol, 2.0 5 eq) is added in portions slowly to a stirred solution of mono-O-benzylidenepentaerythritol (II, Scheme 1 , prepared by the method of Issidorides, C. H.; Gulen, R. C. Organic Syntheses Collected Volume IV, Rabjohn, N., Ed.; John Wiley and Sons: New York, 1963; pp 679-681) (24.11 g, 0.1076 mol) in dry DMF (600 ml_) under a nitrogen atmosphere. The stirred reaction mixture is cooled with an ice water bath for one hour,10 then 1-bromooctane (46.76 ml_, 51.90 g, 0.268 mol, 2.5 eq) is added dropwise over 2 h. After the reaction mixture has been stirred 12 h, another addition of sodium hydride (4.5 g, 0.11 mol, 1.0 eq) and 1-bromooctane (20 ml_, 0.11 mol, 1.0 eq) is made. If after the reaction mixture has been stirred a further 12 h, TLC shows that some mono-O-octyl product is present, another identical addition is made. When all of the mono-O-octyl15 derivative has been consumed, the reaction mixture is quenched by the addition of methanol dropwise until foaming ceases. The reaction mixture is filtered under vacuum and the reaction flask and filter are washed with dichloromethane (~150 ml_). The combined filtrate and washings are concentrated and the residue is extracted with hexanes (300 mL, then 200 ml_). The combined extracts are washed with water (10020 mL), dried (MgSO4) and concentrated under reduced pressure to an oily residue that is passed through a short silica gel column using hexanes, then 5% ethyl acetate/95% hexanes as eluents. The title compound (1a) is a colourless oil (44.71 g, 93 %): RF 0.46 (94 : 6, hexanes : ethyl acetate); 1H NMR (500.13 MHz) delta 0.88, 0.89 (2 t, 6H, J = 6.5 Hz, 2 x Me), 1.20-1.35 (br m, 2OH, 10 x CH2), 1.54, 1.57 (2 pentet, 4H, J = 6.8 Hz, 225 OCH2CH2), 3.22 (s, 2H, eq CCH2O), 3.35 (t, 2H, J = 6.5 Hz, eq octyl OCH2), 3.45 (t, 2H, J = 6.6 Hz, ax octyl OCH2), 3.71 (s, 2H, ax OCH2C), 3.88, 4.09 (2d, 4H, J = 11.5 Hz, H- 4,H-4′, H-6.H-6′), 5.42 (s, 1 H, acetal H), 7.31-7.49 (m, 5H, Ph); 13C NMR delta 138.5 (q Ph) , 128.8 (para Ph), 128.3 (2C, mPh), 126.1 (2C, oPh), 101.7 (acetal C), 71.8 (eq OCH2CH2), 71.7 (ax OCH2CH2), 70.8 (eq OCH2C), 70.2 (C-4 and C-6), 69.4 (ax OCH2C),30 38.9 (q C), 2 x 31.89 (CH2CH2CH3), 29.68, 29.54, 29.51 , 29.45, 2 x 29.34 (6 octyl CH2), 26.22, 26.19 (CH2CH2CH2O), 2 x 22.70 (CH2CH3), 14.3 (Me); MS ESI: CaIc for C28H49O4 449.3631 , found 449.2; calc for C28H48O4Na+ 471.35, found 471.3; calc for (C28H68O4)2Ca2+ 468.34, found 468.5; calc for C28H48O4K+ 487.32, found 487.3.
The synthetic route of 2425-41-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ST. FRANCIS XAVIER UNIVERSITY; MARANGONI, D. Gerrard; GRINDLEY, T. Bruce; JAHAN, Nusrat; PETROPOLIS, Christian; TRAN, Thomas; PAUL, Nawal; WO2010/48715; (2010); A1;,
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