Category: 711-01-3

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. 711-01-3, name is Methyl adamantane-1-carboxylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Under a nitrogen atmosphere, 30.5 g (4.4 mol) of lithium metal (Li) was added to 2 L of tetrahydrofuran (THF) and stirred for 1 hour.Among these, 300 g (2.0 mol) of 2-adamantanone and 258.0 g (3.3 mol) of 2-chloropropane were added to THF 1000.The solution dissolved in mL,It dripped over 30 minutes, cooling so that 20 degrees C or less might be maintained.After completion of the addition, stir at 90 ° C. for 90 minutes,A THF solution of lithium 2-isopropyl-2-adamantyl alcoholate was obtained.362.0 g of methacrylic anhydride in this THF solution(2.4 mol) was dripped over 15 minutes, cooling so that 20 degrees C or less might be maintained. After completion of the dropwise addition, the mixture was stirred at 20 ° C. for 60 minutes to synthesize 2-isopropyl-2-adamantyl methacrylate.After completion of the reaction, 4 L of toluene was added, and further, 2000 mL of 0.2 N aqueous NaOH solution was added, and the mixture was stirred at 20 ° C. for 60 minutes.After removing the aqueous phase, washing was performed twice with 2 L of pure water.By distilling off the solvent from the organic phase,517.0 g (crude yield 99percent, GC purity 84.9percent) of crude 2-isopropyl-2-adamantyl methacrylate was obtained. continue,0.7 g of p-methoxyphenol as a polymerization inhibitor is added to the obtained crude 2-isopropyl-2-adamantyl methacrylate,0.1 kPa, 10 while bubbling dry air from the capillarySimple distillation at 0 to 120 ° C,369.0 g of distilled 2-isopropyl-2-adamantyl methacrylate (GC purity 88.2percent, referred to as ?distillate B?) was obtained.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Osaka Organic Chemical Industry Co., Ltd.; Kojima, Akio; Kono, Naoya; Uenoyama, Yoshitaka; (19 pag.)JP2019/34959; (2019); A;,
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Electric Literature of 711-01-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 711-01-3, name is Methyl adamantane-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A suspension of Lithium Aluminium Hydride (LAH) (6.41 g, 168 mmol) in THF (250 mL) was cooled to 0 C and methyl adamantane-l-carboxylate (21.8 g, 1 12 mmol) in 50 mL of THF was added slowly at 0 C for 30 minutes. After complete addition, the reaction mixture was stirred at room temperature (RT) for 45 minutes. EtOAc (100 mL) was added slowly at 0 C followed by slow addition of water (20 mL) at 0 C. Reaction mixture was filtered and filtrate was dried over anhydrous sodium sulphate, solvent was distilled out and dried to afford the pure product (17 g, 91% yield).

The synthetic route of Methyl adamantane-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LTD.; RAJAGOPAL, Sridharan; THANGAPAZHAM, Selvakumar; PAUL-SATYASEELA, Maneesh; BALASUBRAMANIAN, Gopalan; SHAKTI SINGH, Solanki; KUPPUSAMY, Bharathimohan; KACHHADIA, Virendra; CHENNIAPPAN, Vinoth Kumar; GANESAN, Karthikeyan; NARAYANAN, Shridhar; WO2011/58582; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 711-01-3, 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 711-01-3 as follows.

Example-6; Charge Vitride (sodium dihydro-bis-methoxyethoxy alummate solution in toluene) reducing agent (200 gm) into a dry RBF at 25-35C under nitrogen atmosphere. Cool the Vitrideto 0C-5C. Slowly add toluene (300 ml) into RBF at 0C-5C. Prepare solution of XIII (100 gm) and toluene (200 ml) mixture; add this solution slowly to the reaction mass at 0C-5C. Maintain reaction mass for 10 min at 0C-5C. Raise the temperature to 25C-35C. Maintain the reaction mass for 1 hr at 25C-35C. Check TLC. After TLC complies, cool the reaction mass to 0C-5C. Slowly add saturated ammonium chloride solution to the reaction mass at 0C-5C. Maintain for 10-15 min. at 0C-5C. Filter the salts and wash with toluene (250 ml). Separate the organic layer and aqueous layer. Wash the toluene layer with sodium chloride solution (250ml x 2). Distill toluene out completely under vacuum at or below 70C. Residue weight: 95 gm. (Compound XIV).

According to the analysis of related databases, 711-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; APICORE, LLC; KOVI, Ravishanker; RAPOLE, Keshavrao; NAIK, Ashish; KANNAPAN, Jayaraman; MADALA, Muralikrishna; THAKOR, Sanjay, F.; WO2012/162507; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 711-01-3, name is Methyl adamantane-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H18O2

To 40 g (206 mmol) of methyl 1-adamantanecarboxylate obtained in Production Example 1, 40 g of toluene was added and the atmosphere was replaced with nitrogen, and cooled with refrigerant. While keeping the toluene solution at 10 ° C. or less, 247 g (494 mmol) of methyl magnesium chloride in THF solution (2 M) was added dropwise over 4.5 hours. After that, the temperature was raised naturally and the reaction was carried out at room temperature (25 ° C.) for 3 hours. The reaction solution was again cooled with a coolant, while keeping the temperature below 10°C, 82.3 g (534 mmol) of methacrylic anhydride was added dropwise over 3.3 hours. Thereafter, the temperature was allowed to rise naturally, and the reaction was allowed to proceed at room temperature (25 ° C.) for 3 hours. The measurement results of this crude reaction solution by GC were as follows. Residual material = methyl 1-adamantanecarboxylate: 1.5percent, By-product = 1-(1-adamantyl) -1-methylethanol: 7.3percent and target product=1- (1-adamantyl) -1-methylethyl methacrylate: 91.2percent. While maintaining the crude reaction solution at 25 ° C. or less, magnesium salt was decomposed with hydrochloric acid aqueous solution, the aqueous layer was separated. After washing with 10percent aqueous sodium hydroxide solution and saturated brine, and concentrated. By concentrating the concentrated solution from methanol, 1-(1-adamantyl)-1-methylethyl methacrylate (37 g) was obtained. The isolation yield was 68.5percent. The purity measured by GC was 98.3percent by mass.

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Osaka Organic Chemical Industry Co., Ltd.; Tanaka, Shinji; Uenoyama, Yoshitaka; Kono, Naoya; Ono, Hidetoshi; Kojima, Akio; (11 pag.)JP5993171; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 711-01-3, These common heterocyclic compound, 711-01-3, name is Methyl adamantane-1-carboxylate, 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.

Step 1 compound (10.7 g, 0.055 mmol, 1 equiv) was dissolved in anhydrous THF (150 mL) under argon and was treated with a solution of LiAIH4 (1 M in THF, 69 mL, 69 mmol, 1.25 equiv). After stirring at rt for 1.5 h, the reaction was cooled to 0C and quenched sequentially with H20 (5.1 mL), 15% aq NaOH (5.1 mL), and H20 (10.2 mL). After stirring at rt for 15 min, the slurry was vacuum filtered, and the solids washed with EtOAc (2X100 mL). The filtrate was concentrated by rotary evaporation and the resulting solid purified by flash column chromatography on SILICA GEL (5X15 cm) with 10% ETOAC/CH2CI2. This afforded the Step 2 product as a white solid (8.74 g, 96%).

Statistics shows that Methyl adamantane-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 711-01-3.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/12249; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 711-01-3,Some common heterocyclic compound, 711-01-3, name is Methyl adamantane-1-carboxylate, molecular formula is C12H18O2, 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: A flame-dried round bottom flaskcharged with 40 mmol (4.0 equiv) of 4-bromoanisole in 40 mL THF was cooled to?78 °C and 16 mL BuLi (2.5 M in hexane, 40 mmol, 4.0 equiv) was added dropwisevia syringe. The mixture was stirred for 1.5 h at ?78 °C before the addition of thecorresponding methyl ester (10 mmol, 1.0 equiv), then the mixture was warmed toroom temperature and stirred overnight. After ammonium chloride solutionquenching, the precipitated solid was removed by filtration. The filtrate was extractedwith ethyl acetate (3 × 30 mL), washed with sodium chloride solution, and dried overNa2SO4. After filtration and concentration, the residue was purified by columnchromatography to afford the tertiary alcohol as a white solid.

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pan, Yue; Jia, Kunfang; Chen, Yali; Chen, Yiyun; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1215 – 1221;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 711-01-3, name is Methyl adamantane-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl adamantane-1-carboxylate

To 97 g (499 mmol) of methyl 1-adamantanecarboxylate obtained in Preparation Example 1, 485 g of toluene was added, and nitrogen substitution was carried out, followed by cooling with a refrigerant.While maintaining the toluene solution at 10 ¡ã C. or less, 270 mL (540 mmol) of a solution of methylmagnesium chloride in tetrahydrofuran (THF) (2 M) is added dropwiseThereafter, the temperature was raised naturally, and reaction was performed at room temperature (25 ¡ã C.) for 3 hours.The reaction solution was cooled again with a refrigerant, and 179 g (1160 mmol) of methacrylic anhydride was added dropwise while maintaining the temperature at 10 ¡ã C. or less.Thereafter, the temperature was raised naturally, and reaction was performed at room temperature (25 ¡ã C.) for 3 hours.The crude reaction solution was washed with a 2N aqueous hydrochloric acid solution while keeping the temperature at 25 ¡ã C. or lower, and the aqueous layer was separated.Subsequently, the organic layer obtained is washed with a 10percent aqueous sodium hydroxide solution and saturated brine, and the solvent is evaporated under reduced pressure,Crude 1- (1-adamantyl) -1-methylethyl methacrylate was obtained.(Yield 129.9 g, GC purity 82.3percent)

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Osaka Organic Chemical Industry Ltd.; Kojima, Akio; Kono, Naoya; Uenoyama, Yoshitaka; (20 pag.)JP6478447; (2019); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 711-01-3, 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 711-01-3 as follows.

General procedure: 1 equiv. substrate, 2 equiv. TsCN, 1 equiv CAN, 1 equiv Li2CO3, 0.2 equiv. NHPI and 5 mL DCE were stirred for 16 h at 75 ¡ãC. After 6 h 0.2 equiv. NHPI were added. The reactions mixture was allowed to cool down to room temperature andfiltered over silica gel (50 mL EtOAc, 50 mL MeCN, 50 mL EtOAc).

According to the analysis of related databases, 711-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Berndt, Jan-Philipp; Erb, Frederik R.; Ochmann, Lukas; Beppler, Jaqueline; Schreiner, Peter R.; Synlett; vol. 30; 4; (2019); p. 493 – 498;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 711-01-3, These common heterocyclic compound, 711-01-3, name is Methyl adamantane-1-carboxylate, 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.

Under a nitrogen atmosphere, 30.5 g (4.4 mol) of lithium metal (Li) was added to 2 L of tetrahydrofuran (THF) and stirred for 1 hour.Into this, a solution of 300 g (2.0 mol) of 2-adamantanone and 258.0 g (3.3 mol) of 2-chloropropane dissolved in 1000 mL of THF was added dropwise over 30 minutes while cooling so as to keep 20 ¡ã C. or less. .After completion of the dropwise addition, the mixture was stirred at 20 ¡ã C. for 90 minutes to obtain a THF solution of lithium 2-isopropyl-2-adamantyl alcoholate.To this THF solution, 362.0 g (2.4 mol) of methacrylic anhydride was added dropwise over 15 minutes while cooling so as to keep 20 ¡ã C. or less.After completion of the dropwise addition, the mixture was stirred at 20 ¡ã C. for 60 minutes to synthesize 2-isopropyl-2-adamantyl methacrylate.After completion of the reaction, 4 L of toluene was added, and further 2000 mL of 0.2 N aqueous NaOH solution was added, and the mixture was stirred at 20 ¡ã C. for 60 minutes.After removing the aqueous phase, washing was performed twice with 2 L of pure water.The solvent was distilled off from the organic phase to obtain 517.0 g of crude 2-isopropyl-2-adamantyl methacrylate (crude yield: 99percent, GC purity: 84.9percent).Subsequently, 0.7 g of p-methoxyphenol as a polymerization inhibitor is added to the obtained crude 2-isopropyl-2-adamantyl methacrylate,While distilling dry air from the capillary, carry out simple distillation at 0.1 kPa and 100 to 120 ¡ã C,369.0 g of distilled 2-isopropyl-2-adamantyl methacrylate (GC purity 88.2percent, referred to as ?distillate B?) was obtained.

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Osaka Organic Chemical Industry Ltd.; Kojima, Akio; Kono, Naoya; Uenoyama, Yoshitaka; (20 pag.)JP6478447; (2019); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 711-01-3, name is Methyl adamantane-1-carboxylate, A new synthetic method of this compound is introduced below., Safety of Methyl adamantane-1-carboxylate

In the 10mL single-mouth bottle,Nitrogen protection,97.1 mg (0.50 mmol) of compound 1k is added,2.5mL hexane,105.9 mg (2.25 mmol) deuterated ethanol (EtOD),129.3 mg (2.25 mmol) of sodium reagent (40 wt% dispersion in mineral oil,Particle size 5-10mum),Stir for 5 min at 0C.Rise to room temperatureThe reaction was quenched with 3.0 M aqueous hydrochloric acid.Add ether and saturated brine to extractThe organic phase is dry,Concentrate, column chromatography,79.9 mg of the target compound, 4 gYield 95%.

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Agricultural University; An Jie; Lei Peng; Han Minhui; Ma Xiaodong; Wu Yufei; A Dila¡¤adijiang; Ding Yuxuan; (15 pag.)CN107445798; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics