Sources of common compounds: trans-1,4-Cyclohexanedimethanol

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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3236-48-4, name is trans-1,4-Cyclohexanedimethanol, molecular formula is C8H16O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 3236-48-4

Step D: Preparation of ((lr,4r)-4-(Hydroxymethyl)cyclohexyl)methyl-3- fluorophenyl(phenyl)carbamate.; A suspension of 4-(dimethylamino)- 1 -((3 -fluorophenyl)(phenyl)carbamoyl)-pyridinium chloride (88.25 g, 237 mmol), (lr,4r)-cyclohexane-l,4-diyldimethanol (137 g, 950 mmol) and 4-dimethylaminopyridine (29.0 g, 237 mmol) in acetonitrile (1 L) was heated at 53 0C for 18 h. Upon cooling, the solvent was removed, and the residue was taken up in isopropyl acetate (500 mL) and 1 N HCl (500 mL), heated to suspend all solids, and then filtered through glass fiber filter paper to remove the insoluble bis-carbamate impurity. The aqueous filtrate was discarded, and the organic filtrate was washed with an additional 500 mL of 1 N HCl, followed by water (5 x 500 mL). Heptane (100 mL) was added to the organic phase, which was further washed with water (2 x 500 mL) and brine (100 mL), dried over MgSO4, and concentrated to dryness. The residue was taken up in isopropyl acetate (100 mL) and heptane (300 mL) was added. Crystals gradually formed over 1 h, forming a white precipitate, which was collected by filtration, rinsing with 25percent isopropyl acetate/heptane (100 mL). The filtrate was concentrated to dryness, and the hot residue was taken up in 25percent isopropyl acetate/heptane (100 mL) and filtered hot. As the filtrate cooled, more solids precipitated, which were collected by filtration and combined with the first crop. This material still contained about 5percent bis-carbamate by-product, which could not be readily removed by filtration. The solid was then taken up in dichloromethane (200 mL) and subjected to plug filtration over 1.6 kg of silica gel, eluting the remaining bis-carbamate with dichloromethane and the product with 20percent ethyl acetate/dichloromethane to provide the title compound as a white solid (71 g). LCMS m/z = 358.2 [M+H]+; 1H NMR (CDCl3, 400 MHz) delta 0.91-0.98 (m, 4H), 1.35-1.44 (m, IH), 1.54-1.60 (m, IH), 1.68-1.73 (m, 2H), 1.79-1.83 (m, 2H), 3.45 (d, 7= 6.4 Hz, 2H), 4.01 (d, J= 6.4 Hz, 2H), 6.91 (t, J= 7.6 Hz, IH), 7.04 (d, J = 8.6 Hz, 2H), 7.22-7.30 (m, 4H), 7.38 (t, J = 7.8 Hz, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 3236-48-4.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
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