Category: 3236-48-4

Reference of 3236-48-4 ,Some common heterocyclic compound, 3236-48-4, molecular formula is C8H16O2, 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.

Synthesis ofDIPP-CDM : Anhydrous Na2C03 (8.54 g) was dried in a 250 mL flask for 1.5 h at 180 °C under vacuum. The flask was cooled and flushed with N2. Then, CDM (5.76 g, 40 mmol) and [Ir(cod)Cl]2 (0.97 g) were added. The mixture was dried using several nitrogen- vacuum purging cycles. Then, 24 mL IPPA and 40 mL toluene were added. The mixture was heated at 100 °C. Six hours later, the mixture was cooled and diluted with ether, filtered, and dried under vacuum. The residue was extracted with hexane. Hexane was removed by rotary evaporation. DIPP-CDM (2.7 g) was (0423) recrystallized from ACN twice and dried under vacuum. (0424) The synthesis was confirmed by high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR). It is notable that the acid sensitivity of DIPP-CDM prevents its detection when trifluoro acetic acid, a common HPLC additive, was present in the eluent. Signals of DIPP-CDM were also not observed when CDC13 was used as an NMR solvent, since CDC13 can react with light and oxygen to form phosgene and DC1. It is notable that DIPP was so acid sensitive that DIPP hydrolyzed completely in the silica column even in the presence of triethylamine. In addition, the polarity of DIPP and the transacetate side product during the reaction (such as mono- ester and di-ester substituted compounds) are so similar that they come off of a basic aluminum oxide column together rapidly, leading to the failure of purification. (0425) DIPP-CDM was also purified by column chromatography (CombiFlash® Rf, 100 g HP CI 8, Teledyne Isco, Lincoln, NE, USA). To prevent the hydrolysis of monomer in H20/ACN, 0.1percent TEA was added. C18 column chromatography yielded a higher quantity of polymerization grade monomer (6.8g, 75 wtpercent) than did recrystallization (30 wtpercent). The chemical shifts in the NMR spectra of DIPP-CDM were assigned as below (C6D6 as NMR solvent, Cambridge Isotope Laboratories, Inc., Tewksbury, MA, USA): 1H NMR (C6D6, ppm, 400 MHz): delta 3.93-3.88 (d, = 9.0 Hz, 4H), 3.38-3.35 (d, = 6.65 Hz, 4H), 1.81 (s, 6H), 1.79-1.73 (d, = 6.65 Hz, 4H), 1.61-1.47 (m, 2H), 0.93-0.81 (m, 4H) 13C NMR (C6D6, ppm, 400 MHz): delta 159.88, 80.93, 72.48, 37.51, 29.18, 20.77.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 3236-48-4, trans-1,4-Cyclohexanedimethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHILDREN’S MEDICAL CENTER CORPORATION; KOHANE, Daniel, S.; GUO, Shutao; (110 pag.)WO2017/189953; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3236-48-4, trans-1,4-Cyclohexanedimethanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of trans-1,4-Cyclohexanedimethanol, blongs to alcohols-buliding-blocks compound. Safety of trans-1,4-Cyclohexanedimethanol

Example 1.106: Preparation of Sodium 2-(((lr,4r)-4-(((4- Chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetate.; Method 1.; Step A: Preparation of ((lr,4r)-4-(hydroxymethyl)cyciohexyI)methyl 4- chlorophenyl(phenyl)carbamate.; 4-Chloro-N-phenylaniline (15.0 g, 73.6 mmol), tribasic potassium phosphate, (fine powder, 4.69 g, 22.1 mmol), N^V-carbonyldiimidazole (13.14 g, 81 mmol) and acetonitrile (75 mL) were charged to a 500-mL, jacketed, four-necked cylindrical reaction flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 65 0C under nitrogen and monitored by HPLC. After about 2.5 h HPLC showed > 98% conversion to the intermediate N-(4-chlorophenyl)-N-phenyl-lH-imidazole-l-carboxamide. After about 5.5 h a solution of (lr,4r)-cyclohexane-l,4-diyldimethanol (37.2 g, 258 mmol) in acetonitrile (150 mL) at 65 0C was added to the reaction mixture over 20 min. The resulting mixture was heated at 65 0C overnight. etaPLC showed about 98% conversion to the required product. The mixture was filtered, and the cake was rinsed with acetonitrile (2 x 25 mL). The filtrate was concentrated under reduced pressure (40 0C, 32 torr) 124.125 g of distillate was collected. The residue was diluted with water (50 mL) and this mixture was concentrated under reduced pressure (400C, 32 torr) and 35.184 g of distillate was collected. The residue was diluted with water (50 mL) and the resulting mixture was allowed to stir overnight to give a white paste. The mixture was filtered, and the cake was rinsed with 25% acetonitrile/water (2 x 75 mL). The solid was dried in a vacuum oven to leave a white solid (22.271 g); 94.8% purity by etaPLC peak area. LCMS m/z = 374.3 [M+eta]+; 1H nuMR (400 MHz, DMSO-^6) delta ppm 0.77 – 0.93 (m, 4 H) 1.23 (dd, J = 6.22, 3.51 Hz, 1 H) 1.47 (dd, J = 6.32, 2.91 Hz, 1 H) 1.56 – 1.76 (m, 4 H) 3.20 (t, J= 5.78 Hz, 2 H) 3.92 (d, J = 6.13 Hz, 2 H) 4.33 (t, J = 5.31 Hz, 1 H) 7.28 – 7.35 (m, 5 H) 7.38 – 7.47 (m, 4 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3236-48-4, trans-1,4-Cyclohexanedimethanol, and friends who are interested can also refer to it.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. Formula: C8H16O2

To a 100 mL-flask containing 79 (4.0 g, 27.8 mmol) in DMF (40 mL) was added TBDMSCl (3.56 g, 23.6 mmol) and imidazole (3.79 g, 55.6 mmol). The reaction was allowed to stir at 25 C. for 16 hours after which time saturated aqueous LiBr (50 mL) was added and the reaction extracted with ether (2¡Á50 mL). The ether layers were pooled and extracted again with LiBr (2¡Á35 mL). The ether layer became clear. The ether layer was then concentrated in vacuo and the product purified by flash chromatography, on a silica gel column, eluting with 1:2 ether/petroleum ether to yield 83 (3.80 g, 62%) as a homogenous oil. 1H NMR (CDCl3) delta 3.46 (d, J=6.2 Hz, 2H), 3.39 (d, J=6.2 Hz, 2H), 1.95-1.72 (m, 4H), 1.65 (m, 1H), 1.40 (m, 1H), 1.03-0.89 (m, 4H), 0.88 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3) delta 69.2, 69.1, 41.2, 41.1, 29.5, 26.5, 18.9, -4.8; APCI m/z (rel intensity) 259 (MH+, 100).

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

Reference:
Patent; Rieger, Jayson M.; Linden, Joel M.; Macdonald, Timothy L.; Sullivan, Gail W.; Murphree, Lauren J.; Figler, Robert Alan; Thompson, Robert Douglas; US2006/40889; (2006); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 3236-48-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 3236-48-4, name is trans-1,4-Cyclohexanedimethanol. A new synthetic method of this compound is introduced below.

REFERENCE EXAMPLE 23 Trans-4-benzyloxymethyl-1-hydroxymethylcyclohexane In 10 ml of tetrahydrofuran was suspended 1.51 g of sodium hydride (55percent content), and a solution of 5.0 g of trans-1,4-dihydroxymethylcyclohexane dissolved in 20 ml of tetrahydrofuran was added dropwise thereto with stirring under ice-cooling, and the reaction mixture was stirred at room temperature for 50 minutes. To the reaction mixture was added 3.79 ml of benzyl bromide with stirring under ice-cooling and the mixture was stirred under ice-cooling for 1 hour and further at room temperature overnight. The insolubles were separated by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed successively with an aqueous sodium chloride solution, 10percent aqueous hydrochloric acid solution, an aqueous sodium chloride solution and an aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluding solvent: cyclohexane/ethyl acetate=20/1-5/1) to obtain 1.75 g of the desired compound as a colorless oil. NMR spectrum (CDCl3) delta ppm: 0.85-1.08(4H,m), 1.18-1.30(1H,m), 1.35-1.68(2H,m), 1.72-1.95(4H,m), 3.29(2H,d,J=6.6 Hz), 3.46(2H,t,J=5.3 Hz), 4.50(2H,s), 7.20-740(5H,m)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3236-48-4, trans-1,4-Cyclohexanedimethanol, and friends who are interested can also refer to it.

Reference:
Patent; Sankyo Company, Limited; US5843973; (1998); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts