Category: 124937-73-1

Electric Literature of 124937-73-1, Adding some certain compound to certain chemical reactions, such as: 124937-73-1, name is 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol,molecular formula is C17H20O2, 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 124937-73-1.

EXAMPLE 8 Preparation of tolterodine from 3-(2-hydroxy-5-methyl-phenyl)-3-phenylpropionic acid methyl ester (V) The compound 3-(2-hydroxy-5-methyl-phenyl)-3-phenylpropionic acid methyl ester (44 g 0.163 mol) is refluxed for 24 hours in a mixture consisting of 75 ml of methanol, 75 ml of acetone containing methyl iodide (25 g, 0.175 mol) and potassium carbonate (13.75 g, 0.1 mol). Afterwards, the solid is filtered off and the solvent is evaporated off. The residue is dissolved in ether and washed with water. The solvent is evaporated off to obtain 40 g of an oil which is redissolved in ether (75 ml) and slowly dropped in a solution of lithium aluminium hydride (5.6 g, 0.147 g) in 150 ml of anhydrous ether. The mixture is left under stirring overnight. Afterwards the lithium aluminium hydride excess is destroyed with water and 15% sodium hydroxide. The precipitate is filtered off and solvent is evaporated off to obtain 35 g of an oil corresponding to the propanol derivative. The resulting oil is dissolved in 50 ml of chloroform containing 15 ml of pyridine and the mixture is cooled to -10 C. p-Toluenesulfonyl chloride (14 g, 0.07 mols) is dropped therein and the mixture is reacted at -5/0 C. overnight, then poured in ice/water. The organic phase is separated, washed with diluted hydrochloric acid and distilled under vacuum at a temperature below 50 C. The resulting low-melting solid, that is the tosyl-derivative, is placed in autoclave together with 50 ml of acetonitrile and 50 g of diisopropylamine. After heating the mixture at 80 C. for a week, volatile solvents are evaporated off. The residue is treated with 2N sodium hydroxide and extracted with ether. The product is extracted from the ether phase with a 2N HCl solution. After further washings with ether, the acidic phase is adjusted to basic pH with sodium hydroxide and the product is re-extracted with ether. The organic solution is then evaporated to give an oil (20 g) corresponding to tolterodine phenol-protected as the methyl ether. Said oil is finally dissolved in dichloromethane (75 ml), cooled to 0 C. and treated with a IN solution of boron tribromide in dichloromethane (32 ml 0.032 mols). The mixture is kept one week under stirring in thermocryostat at temperatures ranging from 0 to 5 C. Afterwards, the solvent is evaporated off and the residue is partitioned in a basic water/ether mixture. The organic solvent is evaporated off to obtain an oil which is purified by flash chromatography (eluent hexane-ethyl acetate 7:3) and is tolterodine free base.

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. 124937-73-1, 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DIPHARMA S.P.A.; US2006/189827; (2006); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 124937-73-1, 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. 124937-73-1, name is 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol, molecular formula is C17H20O2, 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.

Example 1: Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenylpropyl methane sulfonate (Vb)This intermediate is of significant importance for use in the preparation of Tolterodine or salts thereof, or its derivatives according to the present invention.In a 3-necked round bottom flask, 6-methyl-4-phenyl-3,4-dihydro coumarin (II, 10Og, 0.420 mol) is charged into methanol (500 ml) at about 250C with stirring. To the resulting suspension, potassium carbonate (K2CO3, 87 g, 0.63 mol) and methyl iodide (MeI, 78 ml, 1.25 mol) are added and the mass is stirred at from about 550C to about 6O0C for 4 h. The reaction mass is cooled to from about 400C to about 450C and MeI (27 ml, 0.43 mol) and K2CO3 (29 g, 0.21 mol) are added. Re-heat the mass to 55~ 6O0C and stir for additional 6 h until the reaction completes. Then solvent is removed by distillation under vacuum. The residue is dissolved in 350 ml of toluene. This organic phase is washed once with 750 ml of DM water and twice with 450 ml of DM water.The organic layer thus obtained is charged into a 3-necked round bottom flask under N2 atmosphere and cooled at temperature from about -50C to about 5C. Toluene solution of sodium bis(2-methoxyethoxy) aluminum hydride (Red-Al, 200 ml, 70% w/v, 0.706 mol) is slowly added through a dropping funnel over a period of 120 min, maintaining the solution temperature within -5 ~ 50C. The mixture is stirred for an additional 1 h at this temperature until the reaction completes. Then aqueous solution of NaOH (80 ml, 10%) is added through a dropping funnel over a period of 45 min, maintaining the temperature at 0 ~ 100C, and continue stirring for an additional 45 min at the same temperature. Add 750 ml of DM water and stir for 30 min at 250C. The biphasic reaction mass is filtered through a celite bed (10 g). The organic layer is collected and dried over 20 g of anhydrous sodium sulfate (Na2SO4). The solids are filtered and washed with 50 ml of toluene. The toluene is distilled off completely and compound IV is obtained as slightly yellow thick oil.The thick oil is dissolved in 300 ml of dichloromethane (DCM) under N2 atmosphere. Triethylamine (Et3N, 90 ml, 0.647 mol) is added and the mass is cooled to 0 ~ 5C. Mesyl chloride (MsCl, 36 ml, 0.465 mol) is added slowly through a dropping funnel over a period of 120 min, keeping the solution temperature below 1O0C. Continue stirring the mixture for an additional 1 h at 0~5C until the reaction completes. 1 L of cold DM water (0~5C) was added and the mass is stirred for 30 ~ 60 min at this temperature. Cone. HCl (25 ml) is added and the mass is stirred until it reaches 25C. The organic layer is collected and washed with 200 ml of DM water. About 180 ~ 220 ml of DCM is distilled off from the organic layer under atmosphere pressure at 38 ~ 43C. 400 ml of cyclohexane is added to the residue and the mass is heated to reflux till a clear solution is obtained (70 ~ 800C). This solution is cooled slowly and compound Vb crystallized. The solid is filtered in Buchner funnel and spray washed with 100 ml of cold cyclohexane. The mass is dried under vacuum at 600C to give 90 ~ 110 g of title compound.

According to the analysis of related databases, 124937-73-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMATHEN S.A.; KOFTIS, Theoharis, V.; NEOKOSMIDIS, Efstratios; SONI, Rohit, Ravikant; MANDALOU, Panagiota; MENISIOU, Aristotelis; WO2010/94292; (2010); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 124937-73-1, 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. 124937-73-1, name is 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol. A new synthetic method of this compound is introduced below.

Dimethylsulfoxide (DMSO) (6.72 ml, 94.6 mmol) in 20 ml of Cl2CH2 was added to a mixture of oxalyl chloride (4.06 ml, 47.3 mmol) in 100 ml of Cl2CH2 and cooled at -78C, always maintaining the reaction temperature under -60C. It was allowed to take place at said temperature for 15 minutes and then a mixture of 3-(2-methoxy-5-methylphenyl)-3-phenylpropanol (9.33g, 36.4 mmol) in 40ml of Cl2CH2 was added. The reaction mixture was maintained for about 45 minutes and triethylamine (25.72 ml, 0.18 mol) was added. The crude reaction product was maintained reacting for about 1 hour and hydrolyzed with 100 ml of NaHCO3 (7%). The extraction was carried out with 100 ml of ethyl acetate. The organic phase was washed with 2x25ml of HCl (5%), dried and evaporated, giving 8.67g (94%) of a viscous orangish liquid containing the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124937-73-1, 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Ragactives, S.L.; EP1698615; (2006); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 124937-73-1, 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. 124937-73-1, name is 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol. A new synthetic method of this compound is introduced below.

Example 1; Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenylpropyl methane sulfonate (Vb); This intermediate is of significant importance for use in the preparation of Tolterodine or salts thereof, or its derivatives according to the present invention.In a 3-necked round bottom flask, 6-methyl-4-phenyl-3,4-dihydro coumarin (II, 100 g, 0.420 mol) is charged into methanol (500 ml) at about 25 C. with stirring. To the resulting suspension, potassium carbonate (K2CO3, 87 g, 0.63 mol) and methyl iodide (MeI, 78 ml, 1.25 mol) are added and the mass is stirred at from about 55 C. to about 60 C. for 4 h. The reaction mass is cooled to from about 40 C. to about 45 C. and MeI (27 ml, 0.43 mol) and K2CO3 (29 g, 0.21 mol) are added. Re-heat the mass to 5560 C. and stir for additional 6 h until the reaction completes. Then solvent is removed by distillation under vacuum. The residue is dissolved in 350 ml of toluene. This organic phase is washed once with 750 ml of DM water and twice with 450 ml of DM water.The organic layer thus obtained is charged into a 3-necked round bottom flask under N2 atmosphere and cooled at temperature from about -5 C. to about 5 C. Toluene solution of sodium bis(2-methoxyethoxy) aluminum hydride (Red-Al, 200 ml, 70% w/v, 0.706 mol) is slowly added through a dropping funnel over a period of 120 min, maintaining the solution temperature within -55 C. The mixture is stirred for an additional 1 h at this temperature until the reaction completes. Then aqueous solution of NaOH (80 ml, 10%) is added through a dropping funnel over a period of 45 min, maintaining the temperature at 010 C., and continue stirring for an additional 45 min at the same temperature. Add 750 ml of DM water and stir for 30 min at 25 C. The biphasic reaction mass is filtered through a celite bed (10 g). The organic layer is collected and dried over 20 g of anhydrous sodium sulfate (Na2SO4). The solids are filtered and washed with 50 ml of toluene. The toluene is distilled off completely and compound IV is obtained as slightly yellow thick oil.The thick oil is dissolved in 300 ml of dichloromethane (DCM) under N2 atmosphere. Triethylamine (Et3N, 90 ml, 0.647 mol) is added and the mass is cooled to 05 C. Mesyl chloride (MsCl, 36 ml, 0.465 mol) is added slowly through a dropping funnel over a period of 120 min, keeping the solution temperature below 10 C. Continue stirring the mixture for an additional 1 h at 05 C. until the reaction completes. 1 L of cold DM water (05 C.) was added and the mass is stirred for 3060 min at this temperature. Conc. HCl (25 ml) is added and the mass is stirred until it reaches 25 C. The organic layer is collected and washed with 200 ml of DM water. About 180220 ml of DCM is distilled off from the organic layer under atmosphere pressure at 3843 C. 400 ml of cyclohexane is added to the residue and the mass is heated to reflux till a clear solution is obtained (7080 C.). This solution is cooled slowly and compound Vb crystallized. The solid is filtered in Buchner funnel and spray washed with 100 ml of cold cyclohexane. The mass is dried under vacuum at 60 C. to give 90110 g of title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124937-73-1, 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; PHARMATHEN S.A.; US2012/41235; (2012); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts