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Chemical Structure| 2850-21-7 Chemical Structure| 2850-21-7
Chemical Structure| 2850-21-7

Ethyl 2-(4-methoxybenzenesulfonyl)acetate

CAS No.: 2850-21-7

4.5 *For Research Use Only !

Cat. No.: A928381 Purity: 95%

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Product Details of [ 2850-21-7 ]

CAS No. :2850-21-7
Formula : C11H14O5S
M.W : 258.29
SMILES Code : O=C(OCC)CS(=O)(C1=CC=C(OC)C=C1)=O
MDL No. :MFCD00054615

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Application In Synthesis of [ 2850-21-7 ]

* 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 [ 2850-21-7 ]

[ 2850-21-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 28743-98-8 ]
  • [ 2850-21-7 ]
YieldReaction ConditionsOperation in experiment
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 nmuol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H20. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 6h; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C, <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly.. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours.. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes.. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 6h; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C, <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 ( 15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 6h; To a stirred solution of 60% chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly.. The reaction mixture tuned cloudy and was stirred at room temperature for 6 hours.. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes.. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 6h; To a seed solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was sied for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield. 100%; MS: 259.1 (M+H)+.
92% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; Part B. (4-Methoxy-benzenesulfonyl)-acetic acid ethyl ester To a solution of mCPBA (18.0 g, 105 mmol) in methylene chloride (50 mL), <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (7.9 g, 35 mmol) in methylene chloride (50 mL) was added dropwise at 0 C. over a period of 20 min. The reaction mixture was stirred at room temperature overnight and then diluted with ethyl acetate (300 mL). The mixture was washed with 1 N NaOH (3*50 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes) to provide the corresponding sulfone (8.3 g, 92%) as colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=7.0 Hz, 2H), 7.03 (d, J=7.0 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 4.08 (s, 2H), 3.90 (s, 3H), 1.22 (t, J=7.1 Hz, 3H); ESI MS m/z 259 [(M+H)+, calcd for C11H15O5S, 259.0].
89% With Oxone; In tetrahydrofuran; methanol; water; at 20℃; for 24h; A solution of oxone (95 g, 0.625 mol) in water (400 mL) was added drop-wise at rt to a solution of Intermediate 18-3 (22 g, 0.097 mol) in a mixture of MeOH (200 ml) and THF (200 ml). After stirring at rt for 24 hours, the reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was extracted with DCM (2x 200 mL). The combined organic layers were washed with water (3x100mL), brine (3x100 mL), dried over Na2SO4, filtered and evaporated in vacuo. The product was dried in vacuo and was used without additional purification (22.3 g, 89 %).
With oxone; In methanol; water; at -5 - 20℃; for 24h; 2nd step: apply the above-mentioned crude product (1g, 6.63mmol) dissolved in 30 ml in methanol, ice-bath cooled to the -5 C following, dropping oxone (8.15g, 13 . 26mmol) of 30 ml aqueous solution, during the dropping control in warm lower than 0 C, then completing, room temperature reaction 24h, adding 50 ml dilution, ethyl acetate (40 ml × 4) extraction, the combined organic phase to saturated NaCl solution (20 ml × 2) washing, to obtained organic phase dried with anhydrous sodium sulfate, filtered, filtrate is decompressed and evaporate solvent to obtain yellow oily liquid 0.8g, crude yield 72%.

 

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