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CAS No. : | 178306-47-3 | MDL No. : | MFCD09833706 |
Formula : | C17H18O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BEPLSLADXOJCBY-UHFFFAOYSA-N |
M.W : | 286.32 | Pubchem ID : | 10541193 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | at 0 - 20℃; for 14 h; | 5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate,Was dissolved in 50 ml of anhydrous methanol,0.1 ml of boron trifluoride etherate was added at 0 ° C.The mixture was stirred at 0 ° C. for 2 hours,The mixture was further stirred at room temperature for 12 hours.The solvent was distilled off, The residue was placed in ethyl acetate,Washed with sodium bicarbonate and water,And dried over magnesium sulfate.After removing the solvent by distillation,5.5 g (88percent) of a pale yellow oil remained. |
84% | at 0℃; for 2 h; | 500 g (2.74 mol) of benzophenone was dissolved in 1200 mL of toluene. After purging with nitrogen, 267 g (4.94 mol) of sodium methoxide was added and the suspension was stirred. The suspension was cooled and a solution of 410 mL (4.68 mol) of methyl chloroacetate in toluene (300 mL) was slowly added dropwise over 90 minutes while maintaining the temperature at -8 to 4 ° C., and then the solution was cooled to -3 to 4 ° C. For 1 hour. After adding 1000 mL of water and stirring for 15 minutes, the organic layer obtained by liquid-liquid separation was washed with 1000 mL of water. The solvent was distilled off under reduced pressure, and the obtained residue (methyl (RS) -3,3-diphenyl-2,3-epoxypropenoate) was dissolved in 1200 mL of methanol and cooled at 0 ° C. to obtain p- A solution of 15 g (0.08 mol) of toluenesulfonic acid monohydrate in methanol (150 mL) was slowly added dropwise over 30 minutes. The mixture was stirred at 0 ° C. for 1.5 hours, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 2500 mL of ethyl acetate and washed twice with 1000 mL of 5percent sodium carbonate aqueous solution. The solvent was distilled off under reduced pressure, 1000 mL of hexane was added to the obtained residue, suspended and stirred at room temperature for 1.5 hours, and then stirred at 0 ° C. for 1 hour. The crystals were collected by filtration and dried under reduced pressure at 60 ° C. for 5 hours to obtain 659 g (yield: 84percent) of methyl (RS) -2-hydroxy-3-methoxy-3,3-diphenylpropanoate. |
75% | Stage #1: for 0.25 h; Stage #2: With toluene-4-sulfonic acid In methanol at 20 - 55℃; for 0.0416667 h; Stage #3: With sodium hydrogencarbonate In methanol; ethyl acetate |
Step-II : preparation of methyl- 2-hydroxy-3-methoxy-3,3-diphenyl propionate (III) :Into a 5L round bottomed flask a mixture of methanol(1.2L) and compound of formula - I (660g) from the previous step were charged and stirred for 15 minutes. p-Toluene sulphonic acid(15g dissolved in 150ml methanol) was slowly added during 30 minutes at 25-55°C. The reaction mass was brought to room temperature, maintained at the same temperature for 2hours was filtered and the filtered compound was dissolved in ethyl acetate(3L). Ethyl acetate layer was washed with 5percent sodium bicarbonate solution(2xlL). Ethyl acetate layer was distilled off completely under vacuum. To the residue hexane(l L) was charged and maintained under stirring for 2hours. The product was filtered and dried at 50-60°C Dry weight : 560g (75percent)Purity by HPLC : 99.9percentMelting range : 100-102°C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | at 100℃; for 1 h; | 500 g (1.75 mol) of (RS) 2-hydroxy-3-methoxy-3,3-diphenyl methyl propanoate Suspended and agitated in 1,000 mL of water, 950 mL (1.90 mol) of 2 mol / L sodium hydroxide was added, and the mixture was stirred at 100 ° C. for 1 hour. The reaction solution was cooled to room temperature, 1500 mL of tert-butyl methyl ether was added, 700 mL of 10percent hydrochloric acid was added, and the mixture was stirred for 20 minutes to dissolve the precipitated solid. After liquid-liquid separation, the organic layer was washed with 1000 mL of water. 1200 mL of heptane was added, and the solvent was distilled off under reduced pressure (200 mmHg) at 40 ° C. to precipitate crystals. 1000 mL of heptane was added, and the mixture was stirred at 0 ° C. for 1 hour. The crystals were collected by filtration and dried under reduced pressure at 40 ° C. for 7 hours,(RS) -2-hydroxy-3-methoxy-3,3-diphenylpropanoic acid 431 g (yield 91percent) was obtained. |
90% | at 90 - 95℃; for 1.5 h; | Step-HI : Preparation of 2-hydroxy-3-methoxy-3,3-diphenyl propionic acid of the formula -(IV) :Into a 5L round bottomed flask a mixture water(l.OL) and compound of formula -III (200g) from step-II were charged and stirred for 15 minutes. IN aqueous sodium hydroxide solution was charged and the reaction mass was stirred for 15 minutes.Reaction mass was heated to 90-95°C and maintained at the same temperature for one hour. The reaction mass was brought to room temperature adjustment of pH was carried out with IN hydrochloric acid solution(1.6L) to 2-3. The product slurry was cooled to 5- 10°C and maintained at the same temperature for 2hours. The product was filtered and dried at 60-65°CDry weight : 172g(90percent)Purity by HPLC : 99.88percentMelting range : 100- 102 °C |
123 g | With water; sodium hydroxide In methanol at 45 - 50℃; for 1 h; | 140 g of methyl 3,3-diphenyloxirane-2-carboxylate was dissolved in 280 ml of methanol and then cooled to 0°C .6.9 ml of BF3OEt2 was added slowly and stirred at 0°C for 2 hours. When the methyl 3,3-diphenyloxirane-2-carboxylate disappears completely and methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate is produced,65.8 g of NaOH was dissolved in 980 ml of water and slowly added dropwise. Methanol (140 ml) was added, the temperature was raised to 45 to 50°C, and the mixture was stirred for 1 hour. When the reaction was completed, the methanol was distilled off under reduced pressure, and diluted with 700 ml of dichloromethane. 300 ml of 6N HCl aqueous solution was added to adjust the pH to 2, and the organic layer was separated. The organic layer was washed with 300 ml of brine, dried, filtered and distilled under reduced pressure, and recrystallized from 500 ml of hexane to obtain 123 g of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid (yield: 82percent). |
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