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3 reactions in Reaxys
2016-05-12 15h:32m:43s (EST)
OH
X Mg
O
+
Search as: As drawn, No salts, No mixtures
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Mg
Br O
OH
Rx-ID: 4579516 View in Reaxys 1/3 Yield 75 %
Conditions & References 4 :4. Reaction of phenylmagnesium bromide with acetone in trihexvKtetradecyl) phosphonium chloride; [00059] To dried ionic liquid trihexyl(tetradecyl) phosphonium chloride (15 .bul.mL), 1 M phenylmagnesium bromide solution in tetrahydrofuran (5.00 mL, 5.00 mmol) was added. To this stirred solution acetone (0.29 g, 5.00 mmol) was added dropwise and allowed to stir for 3 hours and quenched under nitrogen with saturated ammonium chloride followed by water. Hexanes were added to extract 2-phenyl-propan-2-ol and the hexanes extract after drying with anhydrous magnesium sulphate and ionic liquid layer were analyzed by GC-MS giving a total yield of 82percent. Distillation under vacuum was also carried out giving a yield of 75 percent. Stage 1: in Cyphos® IL 101, tetrahydrofuran, Time= 3h Stage 2: With ammonium chloride in Cyphos® IL 101, tetrahydrofuran, water Patent; SIMON FRASER UNIVERSITY; WO2006/7703; (2006); (A1) English View in Reaxys in diethyl ether, Ambient temperature Lomas, John S.; Journal of the Chemical Society. Perkin Transactions 2; vol. 1996; nb. 12; (1996); p. 2601 - 2609 View in Reaxys in diethyl ether, Time= 1h, Ambient temperature Aelterman, Wim; Tehrani, Kourosch Abbaspour; Coppens, Wim; Huybrechts, Tom; De Kimpe, Norbert; Tourwe, Dirk; Declercq, Jean-Paul; European Journal of Organic Chemistry; nb. 1; (1999); p. 239 - 250 View in Reaxys
70 %Chromat.
2 : Example 2 Preparation of α,α-dimethylbenzyl alcohol using CPME as a reaction solvent Example 2 Preparation of α,α-dimethylbenzyl alcohol using CPME as a reaction solvent 45 ml (0.045 mol) of a 1 M phenylmagnesium bromide (PhMgBr) solution in THF was added to a flask, of which the atmosphere had been replaced with nitrogen, and stirred at 0°C for 30 minutes.. A solution of 1.74 g (0.03 mol) of acetone in 50 ml of CPME was slowly added dropwise to the PhMgBr solution at 0°C. After stirring at 0°C for one hour, the reacted mixture was heated to 50°C and stirred for a further one hour.. The reaction mixture was allowed to cool to room temperature and 20 ml of 1 N hydrochloric acid aqueous solution was added to terminate the reaction.. The reaction mixture was analyzed by gas chromatography to confirm that the target α,α-dimethylbenzyl alcohol was obtained in a yield of 70percent. in tetrahydrofuran, CPME, Time= 2.5h, T= 0 - 50 °C Patent; Zeon Corporation; EP1405840; (2004); (A1) English View in Reaxys
85 %Chromat.
22-23 : Example 22 Synthesis of α,α-dimethylbenzyl alcohol using Solvent A 40 parts of a 1 M phenylmagnesium bromide (PhMgBr) solution in Solvent A was added to a flask, of which the atmosphere has been replaced with nitrogen, and stirred at 0°C for 30 minutes. A solution of 1.74 parts of acetone in 70 parts of Solvent A was slowly added dropwise to the PhMgBr solution at 0°C. After stirring at 0°C for one hour, the reaction mixture was heated to 50°C and stirred for a further one hour. After cooling to room temperature, the reaction was terminated with the addition of 20 parts of 1 N hydrochloric acid aqueous solution. The reaction mixture was analyzed by gas chromatography to confirm that the target α,α-dimethylbenzyl alcohol was obtained in a yield of 85percent. 50 parts of water was added to partition the mixture into two layers. The organic layer was removed and distilled under atmospheric pressure using a Vigreux rectification column to obtain 99 parts of fractions distilled at 100-106°C. Gas chromatography analysis confirmed that the distillate contained 99percent or more of CPME. The distillate can be used again as a solvent. in CPME, Time= 2.5h, T= 0 - 50 °C Patent; Zeon Corporation; EP1405840; (2004); (A1) English
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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View in Reaxys 2
H
2H 2H
Mg
2H
2H
Br
2H
O 2H
2H
2H
OH
2H
Rx-ID: 3525198 View in Reaxys 2/3 Yield
Conditions & References
92 %
Kuck, Dietmar; Mehdizadeh, Ahmad; Organic Mass Spectrometry; vol. 27; nb. 4; (1992); p. 443 - 452 View in Reaxys
O
Mg
Br O OH
OH
Rx-ID: 5336059 View in Reaxys 3/3 Yield
Conditions & References in diethyl ether, Addition, Product distribution Holm, Torkil; Journal of Organic Chemistry; vol. 65; nb. 4; (2000); p. 1188 - 1192 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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