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Structure of 76527-25-8

Chemical Structure| 76527-25-8

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Product Details of [ 76527-25-8 ]

CAS No. :76527-25-8
Formula : C16H14O3
M.W : 254.28
SMILES Code : O=C(C1OC1(C2=CC=CC=C2)C3=CC=CC=C3)OC
MDL No. :MFCD09833705

Safety of [ 76527-25-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317
Precautionary Statements:P261-P272-P280-P302+P352-P333+P313-P363-P501

Application In Synthesis of [ 76527-25-8 ]

* 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.

  • Downstream synthetic route of [ 76527-25-8 ]

[ 76527-25-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 67-56-1 ]
  • [ 76527-25-8 ]
  • [ 178306-47-3 ]
YieldReaction ConditionsOperation in experiment
88% With boron trifluoride diethyl etherate; at 0 - 20℃; for 14h; 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 (88%) of a pale yellow oil remained.
84% With toluene-4-sulfonic acid; at 0℃; for 2h; 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 5% 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: 84%) of methyl (RS) -2-hydroxy-3-methoxy-3,3-diphenylpropanoate.
75% 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 25-55C. 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 5% 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 50-60C Dry weight : 560g (75%)Purity by HPLC : 99.9%Melting range : 100-102C
toluene-4-sulfonic acid; at 0 - 35℃; Example-1: Preparation of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester compound of formula-5a:Mixture of benzophenone (100 grams) and methyl chloroacetate (84 grams) in tetrahydrofuran (160 ml) was added to a cooled mixture of tertrahydrofuran and sodium methoxide (51.8 grams) at below -4C in 90 minutes, stirred for 30 minutes at -10C to -5C. The reaction mixture temperature was raised to 25-35C, quenched with water and then extracted with ethyl acetate. The organic layer was washed with brine solution and dried over sodium sulphate. The organic layer was distilled under reduced pressure at 60C and methanol was added to the obtained residue then methanol was distilled off completely. The reaction mixture cooled to 25-35C and methanol (280 ml) was added to it. Paratoluene sulfonic acid (4 grams) was added to the above reaction mixture. The reaction mixture was stirred for 2 hours at 25-35C and then cooled to 0-50C and stirred 45 minutes. The obtained solid was filtered, washed with methanol and then dried at 50-60C to get the title compound. Yield: 110 grams; M.R: 92-96C
With boron trifluoride diethyl etherate; at 0℃; for 2h; 140 g of methyl 3,3-diphenyloxirane-2-carboxylate was dissolved in 280 ml of methanol and then cooled to 0C .6.9 ml of BF3OEt2 was added slowly and stirred at 0C 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 50C, 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: 82%).
5.33 kg With boron trifluoride diethyl etherate;Large scale; The oily product of Example 1 was methyl 3,3-diphenyl-2,3-epoxypropionate (5.54 kg) and methanol (15).L) was charged into the reaction vessel, and boron trifluoride etherate (BF3-ether) (148 ml) was added dropwise.After the reaction is completed, water (15 L) is added to the reaction system to quench the reaction.The reaction mixture was extracted three times with diethyl ether (7 L) and then evaporated.Filter and collect solids,Drying yielded 5.33 kg of methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate in a two step yield of 85%.

  • 2
  • [ 37785-48-1 ]
  • [ 76527-25-8 ]
  • [ 1026105-15-6 ]
  • 3
  • [ 61439-59-6 ]
  • [ 76527-25-8 ]
  • 3-[2-(4-benzyloxy-phenyl)-ethoxy]-2-hydroxy-3,3-diphenyl-propionic acid methyl ester [ No CAS ]
  • 4
  • [ 76527-25-8 ]
  • [ 46112-46-3 ]
  • 4-[2-(2-hydroxy-2-methoxycarbonyl-1,1-diphenyl-ethoxy)-ethyl]-benzoic acid [ No CAS ]
  • 5
  • [ 76527-25-8 ]
  • [ 178306-47-3 ]
YieldReaction ConditionsOperation in experiment
With trifluoroborane diethyl ether; In methanol; ethyl acetate; Example 1 Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate 5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 50 ml of absolute methanol and, at 0 C., 0.1 ml of boron trifluoride etherate was added. The mixture was stirred at 0 C. for 2 h and at room temperature for a further 12 h. The solvent was distilled out, the residue was taken up in ethyl acetate, washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation there remained 5.5 g (88%) of a pale yellow oil.
With trifluoroborane diethyl ether; In methanol; ethyl acetate; EXAMPLE 1 Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate 5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 50 ml of absolute methanol and, at 0 C., 0.1 ml of boron trifluoride etherate was added. The mixture was stirred at 0 C. for 2 h. and at room temperature for a further 12 h. The solution vent was distilled out, the residue was taken up in ethyl acetate, washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation there remained 5.5 g (88%) of a pale yellow oil.
With trifluoroborane diethyl ether; In methanol; ethyl acetate; EXAMPLE 1 Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate 5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 50 ml of absolute methanol, and, at 0 C., 0.1 ml of boron trifluoride etherate was added. The mixture was stirred at 0 C. for 2 h and at room temperature for a further 12 h. The solvent was removed by distillation, the residue was taken up in ethyl acetate, and the solution was washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation, 5.5 g (88%) of a pale yellow oil remained.
  • 6
  • [ 76527-25-8 ]
  • [ 35144-22-0 ]
  • (S)-methyl-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In tetrahydrofuran;Reflux; Large scale; To the reactor was added tetrahydrofuran (19.4 L).Methyl 3,3-diphenyl-2,3-epoxypropionate (4.64 kg),4,6-Dimethyl-2-methanesulfonylpyrimidine (3.32 kg) and potassium carbonate (3.36 kg),Stir well and heat to reflux. After the reaction was completed, water (13.7 kg) was added to the reaction system.The mixture was stirred and separated, and the aqueous layer was separated. Then, 2.5 mol/L potassium hydroxide solution (18.1 L) was added to the reaction system, and the mixture was heated to reflux. After the reaction was completed, tetrahydrofuran was removed, and water (29 L) was added thereto.Dichloromethane (11.7 L), stirred and separated, the methylene chloride layer was separated, the aqueous layer was neutralized with hydrochloric acid to pH 1-5, filtered, and solids were collected and dried to obtain amphetamine (5.9 kg). The yield was 96% and the purity was 99%.
 

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