Category: 765-04-8

Synthetic Route of 765-04-8, 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.765-04-8, name is Undecane-1,11-diol, molecular formula is C11H24O2, molecular weight is 188.3071, as common compound, the synthetic route is as follows.

In a four-necked flask (volume of 1 L) equipped with stirring blades, a thermometer, a dropping funnel and a condenser tube, 300 mL of tetrahydrofuran, 18.8 g (0.10 mol) of undecane-1,1l-diol and 14.4 mg of p-methoxyphenol were charged and dissolved. Subsequently, 9.96 g (0.05 mol) of 2-(2-isocyanatoethoxy)ethyl methacrylate was weighed in a beaker and 150 mL of tetrahydrofuran was added, followed by sufficient stirring and further liquid transfer to the dropping funnel. The four-necked flask was immersed in an oil bath heated to 75 C., and 2-(2-isocyanatoethoxy)ethyl methacrylate was added dropwise so as not to cause boiling of tetrahydrofuran. After completion of the dropwise addition, the reaction was continued for 24 hours while maintaining the temperature of the oil bath, leading to aging. After completion of the aging, the four-necked flask was removed from the oil bath and the reaction product was returned to room temperature, and then HPLC and FT-IR measurements were performed. In that case, a sample obtained by collecting a very small amount of the reaction product using a pipette and removing a solvent using evaporator was used. Analysis conditions of the HPLC measurement are as follows: a column of ZORBAX-ODS, acetonitrile/distilled water of 7/3, a flow rate of 0.5 mL/min, a multi-scanning UV detector, an RI detector and an MS detector. The FT-IR measurement was performed by an ATR method. As a result of the HPLC measurement, peaks of undecane-1,11-diol and 2-(2-isocyanatoethoxy)ethyl methacrylate as raw materials disappeared, and new peak of 2-(2-((((11-hydroxyundecyl)oxy)carbonyl)amino)ethoxy)ethyl methacrylate (molecular weight of 387.52) was confirmed. As a result of the FT-IR measurement, the disappearance of the isocyanate absorption at 2,280 to 2,250 cm-1 and a decrease in intensity of the hydroxy group absorption at around 3,300 cm-1 were confirmed, and the absorption attributed to a urethane group was newly confirmed at 1,250 cm-1. Subsequently, to a tetrahydrofuran solution containing 28.8 g (74.2 mmol) of the precursor compound synthesized by the above-mentioned operation, 15.2 g (74.2 mmol) of (3-isocyanatopropyl)trimethoxysilane was added dropwise while stirring so as not to cause boiling of tetrahydrofuran. In the same manner as in the first stage, a reaction was performed by immersing in an oil bath heated to 75 C. After completion of the dropwise addition, the reaction was continued for 24 hours, leading to aging. After completion of the aging, HPLC and FT-IR measurements were performed. As a result of the HPLC measurement, peaks of 2-(2-((((11-hydroxyundecyl)oxy)carbonyl)amino)ethoxy)ethyl methacrylate and (3-isocyanatopropyl)trimethoxysilane as raw materials disappeared, and new peak of 3,3-dimethoxy-8,22-dioxo-2,9,21,26-tetraoxa-7,23-diaza-3-silaoctacosan-28-ylmethacrylate (molecular weight of 592.80) was confirmed. As a result of the FT-IR measurement, the disappearance of the hydroxy group absorption at around 3,300 cm-1 was confirmed. The chemical structure of the compound synthesized in the present Synthesis Example is mentioned below.

Statistics shows that 765-04-8 is playing an increasingly important role. we look forward to future research findings about Undecane-1,11-diol.

Reference:
Patent; KABUSHIKI KAISHA SHOFU; FUCHIGAMI, Kiyomi; YAMAMOTO, Kenzo; KITADA, Naoya; SHINNO, Kazuya; US2019/300552; (2019); A1;,
Alcohol – Wikipedia,
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Reference of 765-04-8, 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. 765-04-8, name is Undecane-1,11-diol, molecular formula is C11H24O2, 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.

In a 250 mL round bottom flask, 1,11-undecanediol (2.62 g, 14 mmol) was suspended in toluene (50 mL). Glacial acetic acid (8.41 g, 140 mmol), water (2.5 mL), and concentrated sulfuric acid (82 mg, 0.84 mmol) were added, and the reaction mixture was heated to reflux temperature. The progress of the reaction was monitored by GC-MS. After 4 hours of reflux, the flask was removed from the heating bath and allowed to cool to room temperature. The contents of the flask were transferred to a separatory funnel and washed with water (25 mL), 10% sodium bicarbonate (2×25 mL), water (25 mL), and brine (25 mL). The organic phase was dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure to yield 3.08 g (96% yield) of a water-clear liquid, which crystallized on standing at room temperature overnight. Analysis of the final product by gas chromatography-flame ionization detector (GC-FID) (Varian 3600) confirmed the product composition as 73% monoacetate, 14% diol, and 13% diacetate.

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 765-04-8, Undecane-1,11-diol.

Reference:
Patent; Wicki, Markus A.; Nielsen, Kent E.; US2005/143599; (2005); A1;,
Alcohol – Wikipedia,
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Application of 765-04-8, 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 765-04-8, name is Undecane-1,11-diol. This compound has unique chemical properties. The synthetic route is as follows.

A solution of undecane-1,11-diol (14; 1.883 g, 10.00 mmol, 1.00 equiv) in CH2Cl2 (50 mL) at r.t. was treated with TBSCl (1.658 g, 11.00 mmol, 1.10 equiv) and imidazole (1.021 g, 15.00 mmol, 1.50 equiv). The suspension was stirred for 16 h at this temperature, water (25 mL) was added, and the mixture was extracted with CH2Cl2 (3 25 mL). The combined organic phases were washed with water, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The remaining residue was purified by column chromatography (cyclohexane/EtOAc, 9:1) to afford the title compound. Yield: 1.641 g (5.424 mmol, 54%); colourless oil; Rf = 0.55 (cyclohexane/ EtOAc, 3:1). IR (ATR): 3362, 2926, 2855, 1470, 1463, 1388, 1361, 1254, 1098, 1056, 1006, 939, 833, 815, 773, 721, 661 cm-1. 1H NMR (CDCl3, 500 MHz): delta = 3.63 (dt, J = 5.5, 6.5 Hz, 2 H, 1-H), 3.59 (t, J = 6.7 Hz, 2 H, 11-H), 1.60-1.47 (m, 4 H, 2-H, 10-H), 1.38-1.21 (m, 15 H, 3-H to 9-H, OH), 0.89 (s, 9 H, tBu), 0.04 (s, 6 H, Me). 13C NMR (CDCl3, 125 MHz): delta = 63.5, 63.3, 33.03, 32.96, 29.76, 29.74, 29.67, 29.58, 29.57, 26.1, 25.94, 25.88, 18.5, -5.1. HRMS (ESI): m/z [M + H]+ calcd for C17H39O2Si: 303.27138; found: 303.27159.

According to the analysis of related databases, 765-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Petermichl, Markus; Steinert, Christine; Schobert, Rainer; Synthesis; vol. 51; 3; (2019); p. 730 – 738;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts