Category: 707-07-3

707-07-3, name is (Trimethoxymethyl)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of (Trimethoxymethyl)benzene

Raney Ni (1.5 g) is added to a mixture of commercially available nitrogen- containing 4-methyl-3-nitropyridin-2-amine x220 (4.0 g, 26.1 mmol) in methanol (150 ml), and the obtained reaction mixture is hydrogenated in the Parr apparatus at the hydrogen pressure 3 atm until the total conversion of compound x220 is attained for approximately 1.5-2 h. The catalyst is separated by filtration, the filtrate is washed with methanol, and the alcohol solution is evaporated to dryness. The residue is dissolved in sulfolane (10 ml), then PhC(OMe)3 (5.7 g, 1.2 eq, 31.3 mmol) and PTSA (0.3 g) are added, and an air reflux condenser is mounted. The apparatus is argon-blown, and the obtained reaction mixture is heated to 165 0C under vigorous stirring for 10 h. Water (100 ml), saturated aqueous NaHCC>3 (5 ml), and hexane (50 ml) are added to the reaction mixture. The obtained suspension is stirred for 5 min, and the residue is separated by filtration. The residue is washed with water (50 ml) and hexane (100 ml), and vacuum-dried over P2O5 to a constant weight at 45 0C to give 7-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine x221 (2.2 g).Yield: 40 %. LC-MS (MH+): 210.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB S.A.; WO2006/128692; (2006); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, 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.

Methyl 2-oxindoline-6-carboxylate (20 g, 105 mmol) was charged to the reaction vessel. The vessel was equipped with thermometer, stirrer and condenser. Toluene (100 ml, 5 vol) was added followed by acetic anhydride (90 ml, 954 mmol) and the mixture was heated to reflux (115-118 C ). Reflux was continued for 18 hours and a sample was analyzed by HPLC for methyl 2-oxindoline-6-carboxylate (nmt 2.0 a-%). When the methyl 2-oxindoline-6-carboxylate was consumed 40 ml (2 vol) of solvent was distilled off followed by addition of fresh toluene (40 ml, 2 vol). Trimethyl orthobenzoate (53.9 ml, 314 mmol) was added to the boiling reaction during a couple of minutes maintaining the temperature above 110 C . After the addition was complete distillation began and the temperature of the reaction mixture was above 120 C. Eight volumes (160 ml) of solvents were distilled of after which the reaction temperature was adjusted between 110-115 C. The reflux was continued for two hours and precipitation of methyl (E)-l -acetyl-3 -(methoxy(phenyl)methylene)-2- oxoindoline-6-carboxylate began during the reaction. According to HPLC- chromatogram 93.6 % conversion was achieved. The reaction mixture was allowed to cool to room temperature during 5 hours, and then further cooled to 0 C and stirred for two hours at 0 C. The precipitate was filtered and washed with EtOAc (2 x 20 ml, 2 x 1 vol) and dried in vacuum oven at 60 C for 16 hours to obtain the product (33.99 g, 90.85 %, 98.36 a-%) as tan powder. H NMR (400 MHz, DMSO- d6): delta 8.89 (dd, J= 1.5 Hz, J= 0.6 Hz, 1H), 8.0 (dd, J= 8.0 Hz, J= 1.6 Hz, 1H), 7.94 (dd, J= 8.1 Hz, J= 1.6 Hz, 1H), 7.69-7.53 (m, 3H), 7.48-7.33 (m, 2H), 3.93 (s, 3H), 3.76 (s, 3H), 2.57 (s, 3H).13C NMR (l00 MHz, DMSO-d6 ): delta 171.6, 171.3, 167.3, 167.2, 136.8, 131.0, 130.9, 129.1, 128.8, 128.5, 128.1, 126.5, 122.6, 116.7, 106.3, 57.9, 52.2, 27.0.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERMION OY; PIISOLA, Antti; TOIS, Jan; (13 pag.)WO2019/97112; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (Trimethoxymethyl)benzene

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 707-07-3,Some common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, molecular formula is C10H14O3, 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: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Trimethoxymethyl)benzene, its application will become more common.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H14O3

Step A: Methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (922 mg, 3.6 mmol) from Step C of Example 13 was stirred in glacial acetic acid (2.5 mL) and(trimethoxymethyl)benzene (2.0 g, 10.9 mmol) at 70 0C for 3 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate) to give methyl l-(2,2- dimethoxyethyl)-2-phenyl-lH-benzo[J]imidazole-7-carboxylate as a brown oil (1.0 g, 83%): 1H NMR (500 MHz, CDCl3) delta 7.99 (d, J = 8.0 Hz, I H), 7.95 (d, J= 8.0 Hz, I H), 7.72-7.70 (m, 2H), 7.53-7.51 (m, 3H), 7.33 (t, J = 8.0 Hz, I H), 4.76 (d, J= 5.0 Hz, 2H), 4.24 (t, J= 5.0 Hz, I H), 3.99 (s, 3H), 3.07 (s, 6H); MS (ESI+) m/z 341 (M+H).

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; GUZZO, Peter, R.; MANNING, David, D.; EARLY, William; WO2011/8572; (2011); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 707-07-3, 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. 707-07-3, name is (Trimethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a cooled (-78C) solution of 25 (200mg, 0.26mmol), in dry THF (2.6mL), was slowly added a solution of LiAlH4 (2M in THF, 130muL, 0.26mmol). The reaction mixture was stirred 30min at -78C, warmed to room temperature, and stirred 1h at room temperature. The reaction mixture was quenched with saturated aqueous NH4Cl and then extracted with t-BuOMe. The combined organic layer was washed with brine, dried (Na2SO4), and then concentrated under reduced pressure (water bath at room temperature). The residue was dissolved in dry CH2Cl2 (1mL) and CSA (6mg, 0.026mmol) and PhC(OMe)3 (160muL, 1.3mmol) were added. The reaction mixture was stirred overnight at room temperature, quenched with aqueous saturated NaHCO3, and then extracted with CH2Cl2. The combined organic layer was washed with brine, dried (Na2SO4), and then concentrated under reduced pressure (water bath at room temperature) and dried under strong vacuum. The residue was dissolved in dry CH2Cl2 (3mL), cooled at 0C, and then TMSCN (326muL, 2.6mmol) was added followed by the addition of BF3-Et2O (27muL, 0.26mmol). The reaction mixture was stirred 2h at 0C, warmed to room temperature and stirred 2h at room temperature. The reaction mixture was quenched with saturated aqueous NaHCO3 and then extracted with CH2Cl2. The combined organic layer was washed with brine, dried (MgSO4), and then concentrated under reduced pressure. The crude was purified on silica gel (10% t-BuOMe in heptane) to give 4 (160mg, 74%) as a clear viscous oil:

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, (Trimethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Picard, Sebastien; Crich, David; Tetrahedron; vol. 69; 26; (2013); p. 5501 – 5510;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 707-07-3, 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 707-07-3 as follows.

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem