- Synthesis of trans-Stilbene oxide
-
trans- oxide (CAS NO.: ), which is also known as Oxirane, 2,3-diphenyl-, trans, could be produced through the following synthetic routes.
A. Dimethyldioxirane (CAS NO.: )(See Figure 1). A 2-L, three-necked, round-bottomed flask containing a mixture of water (80 mL), acetone (50 mL, 0.68 mol), and sodium bicarbonate (96 g), is equipped with a magnetic stirring bar and a pressure equalizing addition funnel containing water (60 mL) and acetone (60 mL, 0.82 mol). A solid addition flask containing Oxone (180 g, 0.29 mol) is attached to the reaction vessel via a rubber tube. An air condenser (20 cm length) loosely packed with glass wool is attached to the reaction vessel. The outlet of the air condenser is connected to a 75 × 350-mm Dewar condenser filled with dry ice-acetone that is connected to a receiving flask (100 mL) cooled in a dry ice-acetone bath. The receiving flask is also connected in series to a second dry ice-acetone cold trap, a trap containing a potassium iodide solution, and a drying tube. A gas inlet tube is connected to the reaction flask and a stream of nitrogen gas is bubbled through the reaction mixture. The Oxone is added in portions (10–15 g) while the acetone-water mixture is simultaneously added dropwise. The reaction mixture is stirred vigorously throughout the addition of reagents (ca. 30 min). A yellow solution of dimethyldioxirane in acetone collects in the receiving flask. Vigorous stirring is continued for an additional 15 min while a slight vacuum (ca. 30 mm, water aspirator) is applied to the cold trap. The yellow dioxirane solution (62–76 mL) is dried over sodium sulfate (Na2SO4), filtered and stored in the freezer (-25°C) over Na2SO4. The dioxirane content of the solution is assayed using phenyl methyl sulfide and the GLC method. Generally concentrations in the range of 0.07–0.09 M are obtained.
Figure 1B. oxide. To a magnetically stirred solution of trans-stilbene (0.724 g, 4.02 mmol) in 5 mL of acetone is added a solution of 0.062 M dimethyldioxirane in acetone (66 mL, 4.09 mmol) at room temperature. The progress of the reaction is followed by GLC, which analysis indicates that trans-stilbene is converted to the oxide in 6 hr. Removal of solvent on a rotary evaporator gives a white crystalline solid. The solid is dissolved in dichloromethane (CH2Cl2) (30 mL) and dried with anhydrous Na2SO4. The drying agent is filtered off and washed with CH2Cl2. The solvent is removed on a rotary evaporator. Remaining solvent is removed under reduced pressure to give an analytically pure sample of the oxide (0.788 g, 100% yield). Recrystallization from aqueous ethanol gives white plates/prisms, mp 69–70°C .
Notice: Dimethyldioxirane is a volatile peroxide and should be treated as such. The preparation and all reactions of the dioxirane should be carried out in a hood.
Prev:No record
Next:No record - 【Back】【Close 】【Print】【Add to favorite 】
- Related information
- A Synthetic Route of Loperamide oxide
- Synthetic Approach of 6-Methyl-2,3,4,5-tetrahydropyridine N-oxide
- Synthesis of Pyridine-n-oxide
- Production Method of N,N-Dimethyldodecylamine oxide
- Production Method of Mesityl oxide
- Synthetic Approach of trans-4,4'-Dimethoxystilbene
- Preparation of trans-Stilbene
- Systematic Method of Benzofurazan oxide
- Production Method of 3-Methyl-1-phenylphospholene oxide
- Systematic Method of Trimethylene oxide
-
Health and Chemical more >
-
Hot Products
- 7585-39-9 Beta-cyclodextrin
- 681850-23-7 1-(4-Methylphenyl)sulfonyl-4-piperidin-1-ylpiperidine-4-carboxamide
- 89030-95-5 [N2-(N-Glycyl-L-histidyl)-L-lysinato(2-)]copper
- 61789-00-2 Ethylene-propylenerubber
- 80-15-9 Hydroperoxide,1-methyl-1-phenylethyl
- 95-64-7 3,4-Dimethylaniline
- 583-52-8 Potassium oxalate
- 51773-23-0 (+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde
- 240799-53-5 N-(2,2-diethoxyethyl)-N'-[(2-methoxy-3-pyridinyl)carbonyl]urea
- 575-44-0 1,6-Dihydroxynaphthalene
- 24490-79-7 2-Propenenitrile,3-(4-pyridinyl)-(9CI)
- 18107-18-1 (TRIMETHYLSILYL)DIAZOMETHANE