Category: 40546-94-9

Some common heterocyclic compound, 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, molecular formula is C16H14O2, 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. Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

Sodium borohydride (0.76 g, 20 mmol) is added in small portions to the cooled solution of 7-methyl-4-phenyl-3,4-dihydrocoumarin (compound of formula I) (0.48 g, 2 mmol) in 20 ml of methanol. The reaction mixture is stirred for 1 h at 0 C and 4 h at room temperature. The reaction mixture is poured into 1 mol/l solution of hydrochloric acid (120 ml) and extracted with ethyl acetate (3 x 70 ml). The combined organic fractions are dried over anhydrous magnesium sulphate and the solvent evaporated to give the product in 70 % yield (0.49 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40546-94-9, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2006/66931; (2006); A1;,
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Application of 40546-94-9,Some common heterocyclic compound, 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, molecular formula is C16H14O2, 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.

Example 17 [0091] A solution of 0.50 g of 6-methyl-4-phenyl-2-chromanone, 2.65 g of N-fluorobenzenesulfonimide, 22 ml of THF and 6.5 ml of toluene, was cooled to -100 C., and 7.34 ml of a 1.0M THF solution of potassium hexamethyldisilazide was added. After raising the temperature to room temperature, an aqueous citric acid solution was added to terminate the reaction, followed by extraction with ethyl acetate, and the solvent was removed. 0.87 g of the obtained product was quantitatively analyzed by 19F NMR, whereby it was confirmed that 3,3-difluoro-6-methyl-4-phenyl-2-chromanone was formed in a yield of 25%. No formation of a monofluoro product was detected. The structural characteristics of the 3,3-difluoro-6-methyl-4-phenyl-2-chromanone are as follows. 19F-NMR (deuterated acetone): -96.5 (bs).

The synthetic route of 40546-94-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Glass Company, Limited; ISHIBASHI, Yuichiro; Matsumura, Yasushi; US2015/175632; (2015); A1;,
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. 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

EXAMPLE 1; Preparation of 3-(2-hydroxy-5-methylphenyl)-3-phenylpropanol (VIII) A basic aqueous solution of sodium borohydride prepared beforehand by dissolving 23.8 g (0.630 moles) of NaBH4 at ambient temperature in 170 ml of H2O and 3.5 ml of 30% wt./vol. NaOH was added dropwise to a suspension of 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one of the formula (II) (100 g, 0.420 moles) in isopropanol (200 ml). Once addition was complete, the temperature was adjusted to 60 C. and the course of the reaction was monitored by TLC (eluent: cyclohexane/acetone: 70/30) until the substrate had completely disappeared. After 5 h, the reaction mixture was cooled to ambient temperature and HCl (2N) was added until a final pH of 7.0 was obtained. Stirring was continued for 30 min at ambient temperature, then the resultant suspension was filtered through a Buchner filter. The filtered solution was concentrated under reduced pressure and the crude residue was crystallised from toluene (280 ml) to yield 87.4 g (yield 86%) of 3-(2-hydroxy-5-methylphenyl)-3-phenylpropanol (VIII) as a white solid.

The synthetic route of 40546-94-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMI SPA; US2006/79716; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 40546-94-9, 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. 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 3,4-Dihydro-6-methyl-4-phenyl-2H-benzopyran-2-ol (IV) 3,4-Dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one (III, EXAMPLE 1, 100.0 g, 420.2 mmol) is added to toluene (500 mL). The mixture is degassed by purging alternately with vacuum and nitrogen and then cooled to -21. Diisobutylaluminumhydride in toluene solution (DIBAL, 1.5 M, 290 mL, 435 mmol) is then slowly added over 2 hr via add funnel while maintaining the reaction temperature at -20 to -25. The reduction is usually done when the DIBAL add is completed. If the reaction is not done additional DIBAL can be added in increments. When the reaction is done (<1% lactone) ethyl acetate (45 mL) is added at -20 to -25 via add funnel. Very little exotherm is observed. Next, citric acid (23%, 500 mL) is added. The mixture is stirred at 45-50 for 1 hr (or stirred overnight at 20-25), the phases are separated, the organic phase is washed with water (2 x 300 mL). The organic phase is concentrated to 250 mL under reduced pressure. Methanol (500 mL) is added, and the mixture is concentrated to 250 mL. The methanol addition and distillation is repeated to give the title compound in methanol solution. This solution is concentrated to a thick oil which crystallizes on standing to give the title compound (as a mixture of diastereomers), IR (neat) 3410, 3020, 2925, 1605, 1498, 1447, 1205 and 1010 cm-1; MS (m/z, EI) = 240 (parent). Rather then isolating and characterizing the title compound, it is normally taken directly into the next step. HPLC (column = zorbax C-8; mobile phase acetonitrile/water (50/50); flow rate = 1 mL/min; wavelength = 240 nm; note - the absorbance of the lactone (III) at 240 nm is approximately 3.5 times greater than the lactol (IV);. The chemical industry reduces the impact on the environment during synthesis 6-Methyl-4-phenylchroman-2-one. I believe this compound will play a more active role in future production and life. Reference:
Patent; PHARMACIA & UPJOHN COMPANY; EP960109; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 40546-94-9 as follows. Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

Example 1[149] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid; [150](H) (HI)[152] [153] A reaction mixture of 0.75 kg 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 55-65C for 2-3 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1-2 hr. After the completion of addition, reaction mixture was stirred at same temperature for 1-2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 70-800C for 3-5 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 1-2 hrs, then filtered &; washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 55-600C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid.[154] (Yield: 0.71 kg, 83%). [155] HPLC Purity: >; 95 %.

According to the analysis of related databases, 40546-94-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALEMBIC LIMITED; PONNAIAH, Ravi; DESAI, Sanjay; SHAH, Chankrakant Chunilal; PATEL, Kalpesh Shantibhai; PAREKH, Viral Maheshbhai; WO2010/92500; (2010); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 40546-94-9 as follows. 40546-94-9

A reaction mixture of 0.75 kg 3,4-dihydro-6-methyl -4-phenyl-2H-benzopyran-2-one, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 60-650C for 2 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1 hr. After the completion of addition, reaction mixture was stirred at same temperature for 2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 800C for 4 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 2 hrs, then filtered & washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 60-650C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid (Yield: 0.71 kg, 83%).[159] HPLC Purity: > 95 %.

According to the analysis of related databases, 40546-94-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALEMBIC LIMITED; PONNAIAH, Ravi; DESAI, Sanjay; SHAH, Chankrakant Chunilal; PATEL, Kalpesh Shantibhai; PAREKH, Viral Maheshbhai; WO2010/46801; (2010); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics