Category: alcohols-buliding-blocks

Reference of 2425-41-4 , The common heterocyclic compound, 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol, molecular formula is C12H16O4, 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.

20 g of 60 wt% NaH (Mw = 24 ? 0, 0.5 mol) were dispersed in 200 mL of dry tetrahydrofuran. 44.8 g of 2- ((2-phenyl) -1,3-dioxocyclohexyl) -1,3-propanediol (Mw = 224.25, 0.2 mol) were dissolved in 400 mL of dry tetrahydrofuran and suspended in NaH at room temperature Liquid, 25-30 C after the addition was continued for 2 hours. Cooled to 10 C, 42.6mol dimethyl sulfate (0.45mol) was added dropwise, after completion of the reaction was continued at room temperature for 4 hours, the reaction was refluxed for 4 hours. The reaction was stopped and 100 mL of water was added dropwise. The organic phase is washed twice with water, dried and filtered. The solvent was distilled off and the residue was distilled under reduced pressure to obtain about 46.3 g of product, yield 92%.

The synthetic route of 2425-41-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sinopec Corporation; Sinopec Corporation Beijing Chemical Institute; Zhou Qilong; Zhang Rui; Song Weiwei; Tan Zhong; Xu Xiudong; Yan Lian; Li Fengkui; Yu Jinhua; Yin Shanshan; (14 pag.)CN104591979; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 149965-40-2, (5-Bromo-2-chlorophenyl)methanol, 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, SDS of cas: 149965-40-2, blongs to alcohols-buliding-blocks compound. SDS of cas: 149965-40-2

To a solution of 5-bromo-2-chlorobenzyl alcohol (3.00 g, 13.6 mmol) in DMF (10 ml) was added under a nitrogen atmosphere imidazole (2.89 g, 42.0 mmol). After cooling to 0 C. tert-butyldimethylchlorsilan (3.37 g, 22.3 mmol) was added and the reaction mixture was stirred for 18 h in a thawing ice bath. It was diluted with water (20 ml) and extracted with EtOAc (20 ml). The aqueous layer was extracted with ethyl acetate (20 ml) and the organic layers were washed with water (20 ml) and brine (20 ml) and were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (4.35 g, 96%) as a colorless liquid. MS m/e: 279.0 [M-tBu]+.

The synthetic route of 149965-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark; US2009/312314; (2009); A1;,
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Application of 23783-42-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tetraethyleneglycol monomethyl ether (2) (10.0 g, 48.0 mmol) and pyridine (84 mL) in CH2Cl2 (170 mL), solid p-toluenesulfonyl chloride (22.0 g, 115.4 mmol) was added portion-wise at -20 C under nitrogen. The resulting reaction mixture was stirred for 2 days at -20 C. Then, the reaction mixture was allowed to warm to room temperature and water (200 mL) was added. The aqueous layer was extracted with CH2Cl2 (150 mL × 3). The combined organic fractions were dried over MgSO4 and the solvent was removed under reduced pressure. The crude product was purified by chromatography on silica (1:1 EtOAc:hexanes; Rf = 0.3) to yield 3 as a colorless oil, 16.4 g, 94%.1H NMR (500 MHz, CDCl3): delta = 7.80 (d, Ar, 2H), 7.34 (d, Ar, 2H), 4.16 (t, 2H), 3.66 (t, 2H), 3.62-3.65 (m, 6H), 3.58 (s, 4H), 3.532-3.56 (m, 2H), 3.34 (s, 3H), 2.43 (s, 3H). 13C NMR (125 MHz, CDCl3): delta = 144.71 (s, CSO2O), 132.94 (s, CH3CCH), 129.74 (s, CHCHCSO2), 127.89 (s, CCHCH), 71.79, 70.57, 70.46, 70.44, 70.38, 70.36, 69.20, 68.52, 58.94 (CH3OCH2), 21.56 (CH3CHCH). Data was consistent with a previously reported compound [5].

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol.

Reference:
Article; Wu, Xinping; Boz, Emine; Sirkis, Amy M.; Chang, Andy Y.; Williams, Travis J.; Journal of Fluorine Chemistry; vol. 135; (2012); p. 292 – 302;,
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Synthetic Route of 112-70-9, 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. 112-70-9, name is 1-Tridecanol. A new synthetic method of this compound is introduced below.

EXAMPLE 2 [00076] The following Example describes the condensation esterification of DDDA using p-toluenesulfonic acid catalyst and the preparation of DDDA diester using a mixture of 50 mole % Telomer alcohol and 50 mole % Exxal 13 followed by a ?dewaxing? hexane extraction to remove the symmetrically fluorinated component from the mixed ester product. [00077] A mixture of 230.3 g DDDA (1.0 mole), 474.64 g Telomer alcohol (1.05 mole), 207.91 g Exxal 13 (1.05 mole), and 1.9 g p-toluenesulfonic acid (0.01 mole) were charged to a reactor fitted with a Dean-Stark trap and condenser. The Dean-Stark trap was filled with additional Exxal 13. The reaction was heated and sparged with nitrogen to remove water. The nitrogen sparge was removed and the reaction heated to 280 C. under vacuum (0.07 kPa). A portion of the crude ester (610 g) was stirred with 1700 g hexane. The hexane solution was decanted and filtered from undissolved, highly fluorinated material. The hexane solution was treated with activated charcoal and filtered, then with basic alumina and filtered again. Hexane was removed by distillation. Elemental analysis of the residue showed 29.56% F, in good agreement with 28.3% F by 1H NMR analysis. [00078] FIG. 3 shows the wear performance of this high-F-content material in 150N oil. The range of fluorine concentrations shown in FIG. 3 corresponds to weight concentrations of diester ranging up to 1%. Samples of 150N containing 0.25% diester (equivalent to 0.07%F) or more were hazy at ambient temperature, due to the limited solubility of the highly fluorinated diester component, RfO(O)C-(CH2)x-C(O)ORf, but were homogeneous at the 80 C. BOCLE test temperature. The response is very non-linear. A very strong anti-wear effect is obtained with only very small concentrations of the additive. The properties of the mixture of 150N oil and additive are much better than the properties expected based on simple linear effects and overall composition. The anti-wear performance achieved in FIG. 3, through use of the non-symmetrical, partially fluorinated diesters of the present invention, without other additives, is comparable to that of fully formulated motor oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112-70-9, 1-Tridecanol, and friends who are interested can also refer to it.

Reference:
Patent; E. I. du Pont de Nemours and Company; US6734320; (2004); B2;,
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Reference of 180205-28-1, 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. 180205-28-1, name is 1-(Aminomethyl)cyclobutanol, molecular formula is C5H11NO, 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.

5-[4-Fluoro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-1,3,4-oxadiazin-2-one (320 mg, 1.22 mmol, Intermediate 66) was dissolved in DMSO (2.0 ml), and 1 – (aminomethyl)cyclobutan-l -ol (247 mg, 2.44 mmol) was added. The mixture was stirred at 100 “C overnight. The reaction mixture was dilut ed with DMSO, filtered and purified by preparative HPLC to give 231 mg (95 % purity, 52 % yield) of the title compound. LC-MS (Method 1): Rt = 1.00 min; MS (ESIpos): m/z = 344 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.546 (0.74), 1.569 (1.05), 1.591 (0.73), 1.637 (0.72), 1.644 (0.54), 1.654 (0.80), 1.665 (0.53), 1.976 (4.50), 1.993 (4.03), 1.998 (5.17), 2.015 (2.05), 2.074 (14.34), 2.518 (1.22), 2.522 (0.84), 3.279 (4.02), 3.291 (4.05), 5.278 (1.45), 5.308 (16.00), 5.527 (3.57), 7.000 (2.21), 7.022 (2.34), 7.746 (3.95), 7.752 (2.30), 7.774 (1.55), 7.779 (1.23), 10.898 (5.51).

According to the analysis of related databases, 180205-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; ELLERMANN, Manuel; GRADL, Stefan, Nikolaus; KOPITZ, Charlotte, Christine; LANGE, Martin; TERSTEEGEN, Adrian; LIENAU, Philip; HEGELE-HARTUNG, Christa; SUeLZLE, Detlev; LEWIS, Timothy, A.; GREULICH, Heidi; WU, Xiaoyun; MEYERSON, Matthew; BURGIN, Alex; (500 pag.)WO2019/25562; (2019); A1;,
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Application of 2615-15-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 2615-15-8, name is 3,6,9,12,15-Pentaoxaheptadecane-1,17-diol. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Preparation of 3,6,9,12,15-pentaoxaheptadecane-1,17-diol ditosylate A solution of 73.91 g of p-toluenesulfonyl chloride (0.389 mol) in 400 mL of methylene chloride is added dropwise with stirring over a 2.5 hrs period to 400 mL of methylene chloride containing 50 g of hexaethylene glycol (0.177 mol) and 64 mL of triethylamine (39.36 g, 0.389 mol) at 0 C. The mixture is stirred for one hr at 0 C. and heated to ambient temperature for 44 hrs. The mixture is filtered and the filtrate concentrated in vacuo. The resulting residue is suspended in 500 mL of ethyl acetate and filtered. The filtrate is concentrated in vacuo to a yellow oil which was triturated eight times with 250 mL portions of warm hexane to remove unreacted p-toluenesulfonyl chloride. The resulting oil is then concentrated under high vacuum to yield 108.12 g of a yellow oil (quantitative yield). Analysis: Calculated for C26 H38 O11 S2: Calc.=C, 52.87; H, 6.48. found: C, 52.56; H, 6.39. PMR (“proton magnetic resonance”): (60 MHz, CDCl3) delta: 2.45 (s, 6H); 3.43.-3.8 (m, 20H); 4.2 (m, 4H); 7.8 (AB quartet, J=8 Hz, 8H). IR (“infrared”): (neat) cm-1: 2870, 1610, 1360, 1185, 1105, 1020 930, 830, 785, 670.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 2615-15-8, 3,6,9,12,15-Pentaoxaheptadecane-1,17-diol.

Reference:
Patent; Applied Gene Technologies, Inc.; US6379930; (2002); B1;,
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Electric Literature of 25574-11-2, 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 25574-11-2 as follows.

3-(4-Bromophenyl) propan-1-ol (4 g, 18.5 mmol, 1.0 equiv) was dissolved into dichloromethane (60 mL) and cooled to 0C. PCC (5.21 g, 24.1 mmol, 1.5 equiv) was added in portions and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through celite bed and the filtrate was concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (10-20 % diethyl ether/n-pentane) to afford the desired product 5.21a (3.05 g, 76.9 % yield). 1H NMR (400 MHz, CDCI3) 69.83 (s, 1H), 7.43 (d, J = 8.3 Hz, 2H), 7.10 (d, J 8.2 Hz, 2H), 2.94 (t, J 7.3 Hz, 2H), 2.79 (t, J 7.4 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,25574-11-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Jiping; LEE, Patrick; MADERA, Ann Marie; SWEENEY, Zachary Kevin; WO2015/66413; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.107859-98-3, name is Ethyl 3-(4-(hydroxymethyl)phenyl)propanoate, molecular formula is C12H16O3, molecular weight is 208.25, as common compound, the synthetic route is as follows.SDS of cas: 107859-98-3

Example 40 Ethyl 3-{4-[(methoxymethoxy)methyl]phenyl}propanoate A tetrahydrofuran solution (16 mL) of the compound (1.64 g) as produced in Example 2 was admixed with triethylamine (1.6 mL) and chloromethylmethylether (0.71 mL), followed by stirring at room temperature for one day. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The resultant residue was purified on a silica gel column chromatography (n-hexane:ethyl acetate = 4:1) to give the subject title compound (1.47 g) showing the below-described physico-chemical values. TLC: Rf 0.43 (n-hexane:ethyl acetate = 3:1); 1H-NMR (CDCl3): d 1.24, 2.57-2.65, 2.95, 3.41, 4.13, 4.56, 4.70, 7.19, 7.28.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107859-98-3, Ethyl 3-(4-(hydroxymethyl)phenyl)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1785421; (2007); A1;,
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Related Products of 100058-61-5, 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. 100058-61-5, name is 3-(Benzyloxy)cyclobutanol. A new synthetic method of this compound is introduced below.

To a solution of anti-3-(benzyloxy)cyclobutan-1-ol (3.65 mmol, 650 mg) in dry DMF (8 mL) was added 60% sodium hydride(5.47 mmol, 1.5 equiv.) portion wise at 0 C. After the mixture was stirred at 0 C for 15 min, iodomethane (7.29 mmol, 454 muL) was added dropwise at 0 C. The reaction mixture was stirred at room temperature (~ 25 C) for 1-2 h. The mixture was quenched with saturated aqueous of NH4Cl (10 mL), diluted with water (20 mL), extracted with ethyl acetate (20 mL × 2), washed with brine (20 mL), the organic layer was concentrated under reduced pressure, and the crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 60:1 as eluent) to give ((anti-3-methoxycyclobutoxy) methyl) benzene (513 mg, 73 % yield) as colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100058-61-5, 3-(Benzyloxy)cyclobutanol, and friends who are interested can also refer to it.

Reference:
Article; Sheng, Ren; Yang, Liu; Zhang, Yanchun; Xing, Enming; Shi, Rui; Wen, Xiaoan; Wang, Heyao; Sun, Hongbin; Bioorganic and Medicinal Chemistry Letters; vol. 28; 15; (2018); p. 2599 – 2604;,
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Application of 55489-58-2 ,Some common heterocyclic compound, 55489-58-2, molecular formula is C13H20O4, 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.

tert-But l l-phenyl-2,5,8,ll-tetraoxatridecan-13-oate Potassium tert-butoxide (commercially available from for example Aldrich) (7.71 g, 69 mmol) was added to a stirred solution of 2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethanol (commercially available from for example Fluorochem) (15 g, 62 mmol) in tert-butanol (200 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was cooled to 0C, tert-butyl 2- bromoacetate (commercially available from for example Aldrich) (17 mL, 112 mmol) was added, and the mixture was stirred at room temperature overnight. DCM (300 mL) was added ant the organic phase was washed with water (300 mL) and then brine (2 x 200 mL). The organic extract was dried using a hydrophobic frit and concentrated under reduced pressure to give the crude product as a yellow oil. The product was purified by chromatography on silica using a gradient elution from 0% to 100% methyl tert-butyl ether in cyclohexane to afford the title compound (13.3 g, 38 mmol, 60% yield). LCMS RT= 1.10 min, ES+ve m/z 372.4 [M+NH4]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55489-58-2, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMPOS, Sebastien, Andre; HARLING, John, David; MIAH, Afjal, Hussain; SMITH, Ian, Edward, David; WO2015/867; (2015); A1;,
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