Month: November 2020

Adding some certain compound to certain chemical reactions, such as: 349-75-7, name is (3-(Trifluoromethyl)phenyl)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 349-75-7. 349-75-7

General procedure: Catalyst preparation: Iron(III) nitrate (112.5 mg, mmol) is added to acetone (2 mL)and the mixture is stirred vigorously in the presence of air for 5 min until complete dissolution of the complex. Bentonite (150 mg) is then added and the resulting suspension stirred for another 5 min. Thus, the solvent is eliminated under reduced pressure on a water bath at 50C (rotary evaporator). After 15 min, the catalyst isobtained as a brown powder. Warning: it is important not to evaporate solvent at higher temperatures (>50 C) orfor longer periods of time (>1 h), which leads to an unstable reagent, which will decompose exothermally in 1-2 h with evolution of nitrogen dioxide. Therefore, wealways prepared the amount of catalyst just necessary for our experiment and immediately engaged it in the oxidation reaction. This takes only 30 min to prepare the catalyst and avoids problem of deactivation. Sequential reaction: 1.5 mL of CH2Cl2 and benzylic alcohol (0.5 mmol) were added tothe just prepared catalyst and stirred until completion (around 4h) at 35C. Then,heating was stopped and the homoallylic alcohol (0.5 mmol) and trimethylsilylchloride (80 L, 0.6 mmol) were added and the reaction mixture was stirred for two hours at room temperature. The crude mixture was then directly chromatographied to give the desired THP with good yield over the two steps RMN 1H (300 MHz, CDCl3) 7.73 – 7.40 (m, 4H), 4.40 (dd, J = 11, 2 Hz, 1H), 4.22 (ddd, J = 12, 5, 2 Hz, 1H),4.17 (tt, J = 12, 5 Hz, 1H), 3.62 (td, J = 12, 2 Hz, 1H), 2.41 (m, 1H), 2.18 (m, 1H), 1.99 (qd, J = 12, 6 Hz, 1H),1.86 (q, J = 12 Hz, 1H). 13C NMR (75 MHz, CDCl3) 142.40 , 130.97 (q, J = 32 Hz), 129.22 – 129.16 (m),129.06 , 124.74 (q, J = 4 Hz), 122.74 (q, J = 4 Hz), 122.40 , 78.63 , 67.48 , 55.41 , 44.69 , 36.81 .RMN 19F (282MHz, CDCl3) -62.59. HRMS (CI): calculated for C12H13ClF3O [M+H]+: 265.0602 found 265.0601

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 349-75-7.

Reference:
Article; Fache, Fabienne; Muselli, Mickael; Piva, Olivier; Synlett; vol. 24; 14; (2013); p. 1781 – 1784;,
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349-75-7 ,Some common heterocyclic compound, 349-75-7, molecular formula is C8H7F3O, 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.

Preparation 22-1); 2-[3-Oxo-2-(3-trifluoromethyl-benzyl)-2,3-dihydro-pyridazin-4-yl]-butyricacid ethyl esterThe compound of Preparation 6-6) (100 mg, 0.48 mmol), DIAD(diisopropyl azodicarboxylate, 192 mg, 2.0 eq), (3-trifluoromethyl-phenyl)-methanol (168 mg, 2.0 eq) and triphenylphosphine (312 mg, 2.5 eq) were dissolved in THF (6 mL), and stirred for 2 h at room temperature. The mixture was concentrated under reduced pressure and separated by column chromatography (30% EA/Hexane) to give the title compound (158 mg, 90%).1H-NMR (500MHz, CDCl3) delta 7.76(d, IH), 7.65(s, IH), 7.60(d, IH), 7.53(d, IH), 7.43(t, IH), 7.20(d, IH), 5.40-5.30(ABq, 2H), 4.20-4.08(m, 2H), 3.85(t, IH), 2.01-1.76(two m, 2H), 1.19(t, 3H), 0.94(t, 3H)

According to the analysis of related databases, 349-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG LIFE SCIENCES LTD.; WO2008/16239; (2008); A1;,
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616-29-5 ,Some common heterocyclic compound, 616-29-5, molecular formula is C3H10N2O, 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.

General procedure: The mixture of 1,2,3,4-tetrahydroacridine [38] (3/4; 1 eq) and different diaminoalkanes was heatedin phenol (0.5 eq) at 165-170 C for a period of 35¡À60 min in the presence of potassium iodide ina catalytic amount. After the completion of reactions, monitored on TLC and on consumption ofstarting material, the reaction mixture was allowed to come at room temperature. After cooling, thereaction mixture was dissolved into DCM and washed with 5% NaOH (3 75 mL) and brine solution,respectively. Finally, the DCM layer so obtained was dried over the anhydrous Na2SO4 and thenconcentrated under reduced pressure to give desired product in crude form. The column purificationof the crude product over silica gel (100-200 mesh) in 4-6% methanol/dichloromethane afforded thealkyl substituted tacrine amines (5-10) in a 60-75 % yield and their spectral data are presented in ourprevious publication [23].

According to the analysis of related databases, 616-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rajeshwari, Rajeshwari; Chand, Karam; Candeias, Emanuel; Cardoso, Sandra M.; Chaves, Silvia; Amelia Santos; Molecules; vol. 24; 3; (2019);,
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39590-81-3, 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 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane. This compound has unique chemical properties. The synthetic route is as follows.

a) [1-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]methyl]-cyclopropylmethanol To a solution of 3-(2-cyanophenylsulfonyloxy)-5-methylphenol (1.45 g, 5.0 mmol), as prepared in the step a of example 13), tri-n-butylphosphine (1.62 g, 8.0 mmol) and 1,1-dihydroxymethylcyclopropane (1.52 g, 15 mmol), as prepared in U.S. Patent No. 5,472,964, in anhydrous tetrahydrofuran (50 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.02, 8.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (80 mL) was added to the mixture, and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (10% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.15, 62%). 1H-NMR (300 MHz, CDCl3) delta 8.09 (m, 1H), 7.93 (m, 1 H), 7.80 (m, 2H), 6.66 (s, 1H), 6.60 (s, 1H), 6.56 (s, 1H), 3.86 (s, 2H), 3.60 (s, 2H), 2.26 (s, 3H), 1.85 (br s, 1H), 0.62 (s, 4H).

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 39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane.

Reference:
Patent; Ortho-McNeil Pharmaceutical, Inc.; EP906091; (2006); B1;,
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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. 3360-41-6, name is 4-Phenylbutan-1-ol. A new synthetic method of this compound is introduced below., 3360-41-6

REFERENCE EXAMPLE 23 N,N-dimethyl-4-phenylbutylamine To 1.50 g of 4-phenylbutanol was added 385 mul of phosphorus tribromide with ice cooling, and the mixture was stirred at a room temperature for 5 minutes and then at 80 C. for one hour. To the reaction mixture were added 20 ml of ice water and 30 ml of ethyl acetate. The separated organic layer was, successively washed with water, 5% sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure to obtain an oily residue. The residue was applied to a silica gel column and eluted with hexane/benzene (6:1) to obtain 1.94 g of (4-bromobutyl)benzene as a colorless liquid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3360-41-6, 4-Phenylbutan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Tobishi Yakuhin Kogyo Kabushiki Kaisha; US5093370; (1992); A;,
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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. 4415-82-1, name is Cyclobutylmethanol, molecular formula is C5H10O, 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. 4415-82-1

Step 1 : Into a 20-L 4-necked round-bottom flask was placed a solution of cyclobutylmethanol (1000 g, 1 1 .61 mol) in dichloromethane (10 L). This was followed by the addition of Dess-Martin periodinane (4683 g, 1 1 .04 mol) in several batches at 10-15 C over 120 min. The resulting solution was stirred for 2 h at room temperature and then quenched by the addition of 20 L of cold, saturated aqueous sodium bicarbonate solution. Solids were removed by filtration and washed with 5 L of dichloromethane. The filtrate was extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with DCM:PE (2:1 ). This resulted in 100 L of cyclobutanecarbaldehyde in dichloromethane and petroleum ether solution.

The chemical industry reduces the impact on the environment during synthesis 4415-82-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DINSMORE, Christopher; FRADERA LLINAS, Francesc Xavier; KUDALE, Amit Ashokrao; MACHACEK, Michelle; REUTERSHAN, Michael Hale; THOMPSON, Christopher Francis; TROTTER, B. Wesley; YANG, Liping; ALTMAN, Michael, D.; BOGEN, Stephane, L.; DOLL, Ronald, J.; VOSS, Matthew, E.; WO2014/100071; (2014); A2;,
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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 107-75-5, name is 7-Hydroxy-3,7-dimethyloctanal. This compound has unique chemical properties. The synthetic route is as follows. 107-75-5

General procedure: Aldehyde (2 equiv) was added to a mixture of N-acyl phthalimide (1 equiv), potassium phthalimide (20 mg, 0.11 mmol, 0.2 equiv), NaI (16 mg, 0.11 mmol, 0.2 equiv), 4 A MS (100 mg), MeCN (0.53 mL), and EtOAc (0.53 mL) at room temperature with stirring. After 24 h, the mixture was diluted in Et2O, and sequentially washed with satd aq NH4Cl (1¡Á), 1 M aq NaOH (3¡Á), and brine (1¡Á). The organic phase was dried (MgSO4) and concentrated. The crude material was purified by normal phase flash chromatography using a mixture of hexanes/EtOAc eluent.

Statistics shows that 107-75-5 is playing an increasingly important role. we look forward to future research findings about 7-Hydroxy-3,7-dimethyloctanal.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
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Adding some certain compound to certain chemical reactions, such as: 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin, 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 575-03-1. 575-03-1

General procedure: The appropriate bromoketone (6a-o) (1.7 mmol) and triethylamine (1.6 mmol) were added to as olution of either7-hydroxy-4-methyl-2H-chromen-2-one 4 (1.4 mmol)or 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one 5 (1.4 mmol) in THF (20 mL). The mixture was stirred at room temperature for 24h, filtered and the solvent was evaporated under reduced pressure.The solid residue was purified by column chromatography eluting with DCM/MeOH 9:1 to afford (7a-n) and (8a-o).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 575-03-1.

Reference:
Article; Kandil, Sahar; Westwell, Andrew D.; Mcguigan, Christopher; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2000 – 2004;,
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Adding a certain compound to certain chemical reactions, such as: 626-18-6, 1,3-Benzenedimethanol, 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, 626-18-6, blongs to alcohols-buliding-blocks compound. 626-18-6

To a stirred solution of 1, 3-phenylenedimethanol (1) (5 g, 36.496 mmol) in THF (100 mL) was treated with NaH (1.17 g, 29.197 mmol) at 0C to RT for 30 min. Ethyl iodide (2.3 ml, 29.197 mmol) in THF (10 mL) was added to above reaction mixture at OC and stirred at 50 C for 16h under nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with ethyl acetate (3x100mL). Combined organic layers were washed with brine (2×100 mL) and dried over Na2SO4, evaporated under reduced pressure. Crude residue was purified by Combi-flash chromatography using 20 % ethyl acetate in pet-ether to afford (3-(ethoxy methyl) phenyl) methanol 3 (2.1g, 12.65 mmol, 34 % yield) as a yellowish oily liquid. TLC system: 40 % ethyl acetate in pet-ether – Rf: 0.50; LCMS: m/z = 120.99 (M-46) +

With the rapid development of chemical substances, we look forward to future research findings about 626-18-6.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; FEESE, Michael, David; LEE, Sam, Sk; (249 pag.)WO2018/200425; (2018); A1;,
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623-72-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 623-72-3, name is Ethyl 3-Hydroxypropanoate. This compound has unique chemical properties. The synthetic route is as follows.

Example 16 This example describes the preparation of various alkyl acrylate esters by dehydrating 3-HP esters using various catalysts. A catalyst was placed in a 3-neck flask that was equipped with a temperature probe (in contact with the catalyst). A distillation column and receiving flask were attached so that the vapors formed during the reaction could be collected, and the catalyst was heated to the desired temperature. A solution of a 3-hydroxypropionic acid ester in the corresponding alcohol was added drop-wise directly onto the catalyst using a syringe. The liquid that distilled over was collected and analyzed by gas chromatography. The results, and corresponding experimental conditions are shown in the following table. Ester Catalyst Temperature Concentration Solvent Yield of Yield of (C) of Ester in Acrylic Acrylic Solvent ester (GC) acid (GC) – (%) (%) (%) Ethyl NaH2P04-Silica 275-EtOH 49 26 Ethyl NaH2PO4-Silica 250 35 EtOH 53 Ethyl NaH2PO4-Silica 250 50 EtOH 14 21 Ethyl NaH2PO4-Silica 180 40 EtOH 30 – Ethyl Copper-H3PO4 220 20 EtOH 50 50 Methyl NaH2PO4-Silica 280-MeOH 78 Methyl CuS04-Silica 280-MeOH 37 9 Methyl Cs2CO3-Silica 220 45 MeOH 49 – Butyl NaH2PO4-Silica 280 50 BuOH 40 Similar dehydration reactions were performed using 3-HP as the starting material and a flask containing heated catalyst in place of the GC: (a) Aqueous 3-HP was dehydrated to acrylic acid over NaH2PO4-Silica gel catalyst at 180C. Based on GC and HPLC analysis, the yield of acrylic acid was 90- 96%. (b) Aqueous 3-HP was dehydrated to acrylic acid over H3PO4-Silica gel catalyst at 180C. Based on GC and HPLC analysis, the yield of acrylic acid was 85-90%. (c) Aqueous 3-HP was dehydrated to acrylic acid over CuS04-Silica gel catalyst at 180C. Based on GC and HPLC analysis, the yield of acrylic acid was 73%. (d) Aqueous 3-HP was dehydrated to acrylic acid over Zeolite H-ss powder and 85% H3PO4 as the catalyst at 180C. Based on GC and HPLC analysis, the yield of acrylic acid was 71%. (e) Aqueous 3-hydroxyisobutyric acid was dehydrated to methacrylic acid over NaH2PO4-Silica gel catalyst at 270C. Based on GC analysis, the yield of methacrylic acid was 79%.

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 623-72-3, Ethyl 3-Hydroxypropanoate.

Reference:
Patent; CARGILL, INCORPORATED; WO2003/82795; (2003); A2;,
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