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11 reactions in Reaxys
2018-02-23 17h:50m:00s (EST)
O
1. Query O
Search as: As drawn
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HO Br
O
O
O O
HO
Rx-ID: 3804948 View in Reaxys 1/11 Yield
Conditions & References With potassium carbonate in acetone McKervey, M. Anthony; Ye, Tao; Journal of the Chemical Society, Chemical Communications; nb. 11; (1992); p. 823 - 824 View in Reaxys 1 : Preparation of 2-ethoxy benzoic acid ethyl ester In a round bottom flask having two openings, 10 mmol of 2-hydroxy benzoic acid was poured at room temperature. Then, 50 ml of dimethylformamide was introduced into the flask. As a catalyst, K2C03 (24 mmol) was introduced into the flask, and bromo ethane (24 mmol) was slowly added dropwise thereto. Afier finishing dropping, the mixture was reacted at room temperature for 6 hours. 500 ml of purified water was added to the reactant, and extraction was executed using 100 ml ofn-hexane. Afier drying the hexane layer under reduced pressure, separation and purification were executed using silica gel colunm chromatography (ethyl acetate:hexane=1 :50) to produce 2-ethoxy benzoic acid ethyl estet The obtained product was subjected to identification by fast atom bombardment mass spectroscopy (FAI3-MS).FAR mass: 195 [M+H] With potassium carbonate in N,N-dimethyl-formamide, Time= 6h, T= 20 °C Patent; RNS CO.,LTD.; KIM, Cheong Taek; (16 pag.); US2016/221921; (2016); (A1) English View in Reaxys 1 : Preparation of 2-ethoxybenzoic acid ethyl ester In a two-neck round flask, 10 mmol of 2-hydroxybenzoic acid was added at room temperature, and 50 ml of dimethylformamide was added thereto. 24 mmol of potassium carbonate (K2CO3) was added as a catalyst, and then bromoethane(Bromo ethane) (24 mmol) was slowly added dropwise. After addition, the reaction was allowed to proceed at room temperature for 6 hours. 500 ml of purified water was added to the reaction mixture and extracted with 100 ml of n-hexane. The hexane layer was dried under reduced pressure and then separated and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 50) to obtain 2-ethoxybenzoic acid ethyl ester. FAB-MS). With potassium carbonate in N,N-dimethyl-formamide, Time= 6h, T= 20 °C Patent; RNS Co., Ltd; Kim, Chung Taek; (22 pag.); KR2015/29273; (2015); (A) Korean View in Reaxys
HO NH 2
O
O
O O
HO
Rx-ID: 43808834 View in Reaxys 2/11 Yield 91 %
Conditions & References 3 : Example 3 In the is provided with an agitator, reflux condenser, dropping funnel in the reaction container, adding salicyate (2) 0.32mol, the mass fraction is 35percent sodium bisulfite solution 0.65mol, stannous chloride 0.31mol, the mass fraction of 20percent sodium chloride solution 300 ml, control the stirring speed 170rpm, reducing the temperature of the solution to 9 °C, ethane instillment amine (3) 1.33mol, stirring continued after adding 9h, by adding the mass fraction is 60percent cyclohexane 300 ml, after 120 min, separating the organic layer, potassium nitrate solution washing 5 times, water-free magnesium sulfate dehydration, vacuum distillation, collecting 105 - - 115 °C fraction, the mass fraction of the 95percent isopropanol in recrystallization, to obtain crystal O-ethoxy ethyl formate 56.49g, yield 91percent. With sodium hydrogensulfite, sodium chloride, tin(ll) chloride, Time= 9h, T= 9 °C , Temperature
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Patent; Chester Beijing Science And Technology Co., Ltd.; Peng, Fei; (5 pag.); CN105503586; (2016); (A) Chinese View in Reaxys
O OH
OH O
O
O
O
Rx-ID: 29757232 View in Reaxys 3/11 Yield
Conditions & References With thionyl chloride, Time= 0.0666667h, Microwave irradiation Wang, Xiao Qing; Zhao, Zhi Gang; Liu, Xing Li; Li, Wei Jie; Journal of Chemical Research; nb. 6; (2010); p. 307 309 View in Reaxys Li, Xiaorui; Zhao, Zhigang; Li, Guohua; Shi, Peiyu; Journal of Chemical Research; nb. 7; (2010); p. 410 - 413 View in Reaxys With sulfuric acid, Reflux Zheng, Qing-Zhong; Zhang, Xiao-Min; Xu, Ying; Cheng, Kui; Jiao, Qing-Cai; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 18; nb. 22; (2010); p. 7836 - 7841 View in Reaxys With thionyl chloride, Time= 0.0666667h, Microwave irradiation Li, Xiaorui; Zhao, Zhigang; Cheng, Yuyu; Li, Hui; Journal of Chemical Research; vol. 35; nb. 4; (2011); p. 234 237 View in Reaxys With thionyl chloride Li, Xiaorui; Qiu, Liying; Mei, Qinggang; Bi, Qingwei; Zhao, Zhigang; Journal of Chemical Research; vol. 35; nb. 6; (2011); p. 364 - 367 View in Reaxys With thionyl chloride, Microwave irradiation Yang, Jie; Zhao, Zhigang; Li, Hui; Journal of Chemical Research; vol. 36; nb. 7; (2012); p. 383 - 386 View in Reaxys With sulfuric acid Du, Qian-Ru; Li, Dong-Dong; Pi, Ya-Zhou; Li, Jing-Ran; Sun, Jian; Fang, Fei; Zhong, Wei-Qing; Gong, HaiBin; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 21; nb. 8; (2013); p. 2286 - 2297 View in Reaxys
O
Cl O
O
O
O
O
Rx-ID: 33825056 View in Reaxys 4/11 Yield 70 %
Conditions & References With zinc(II) chloride, Time= 12h, T= 25 °C Yu, Yun-Feng; Gao, Jian-Rong; Jiang, Shao-Liang; Han, Liang; Jia, Jian-Hong; Li, Yu-Jin; Asian Journal of Chemistry; vol. 24; nb. 11; (2012); p. 5199 - 5201 View in Reaxys
Copyright © 2018 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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O
HO
O
O
O
O
O
S
O
O
HO
Rx-ID: 3804951 View in Reaxys 5/11 Yield
Conditions & References
80 %
To a stirred solution of Salicylic acid (50 g, 143 mmol) in acetone (300 mL) was added anhydrous powdered potassium carbonate (80 g, 580 mmol). Diethyl sulfate (44.25 g, 290 mmol) was added in portions for about 10 min at room temperature. After the addition was complete, the solution was heated to reflux temperature on a water bath and maintained for 3 h. The solution was cooled to room temperature and then concentrated under reduced pressure. Distilled water (200 mL) was added to the reaction mixture, which was then extracted with ethyl acetate (200 mL). The organic layer was washed with distilled water (2.x.200 mL), dried over anhydrous sodium sulfate, and concentrated to yield the title Ethyl 2-Ethoxy-benzoate (45 g, 80percent). With potassium carbonate in acetone, Time= 3.16667h, T= 20 °C , Heating / reflux Patent; Kundu, Tapas Kumar; Balasubramanyam, Karanam; Swaminathan, Vankatesh; US2006/167107; (2006); (A1) English View in Reaxys With potassium hydroxide, tetrabutylammomium bromide, 1.) 60 deg C, 0.1 Torr, 6 h, 2.) room temp., 24 h, Yield given. Multistep reaction Barry, J.; Bram, G.; Decodts, G.; Loupy, A.; Orange, C.; et al.; Synthesis; nb. 1; (1985); p. 40 - 45 View in Reaxys
O
OH
O
Br
O
O
O
Rx-ID: 4553568 View in Reaxys 6/11 Yield
Conditions & References With potassium carbonate in acetone Sadashiva, Bukkinakere K.; Prasad, Veena; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 4; (1996); p. 755 - 760 View in Reaxys
O
O
O
Rx-ID: 7655299 View in Reaxys 7/11 Yield
Conditions & References Salicylsaeure, Diaethylsulfat McKillop et al.; Tetrahedron; vol. 30; (1974); p. 1379,1380 View in Reaxys
I
O
dipotassium compound of/the/ salicylic acid
O
O
Rx-ID: 7655300 View in Reaxys 8/11
Copyright © 2018 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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Yield
Conditions & References With ethanol, unter Druck Foelsing; Chemische Berichte; vol. 17; (1884); p. 486 View in Reaxys Goettig; Chemische Berichte; vol. 9; (1876); p. 1474 View in Reaxys
HO
I
O
O
potassium hydroxide
O
O
HO
Rx-ID: 5812210 View in Reaxys 9/11 Yield
Conditions & References T= 160 °C , im geschlossenen Rohr Goettig; Chemische Berichte; vol. 9; (1876); p. 1474 View in Reaxys
O
I
potassium compound of salicylic acid ethyl ester
O
O
Rx-ID: 7655301 View in Reaxys 10/11 Yield
Conditions & References T= 160 °C , im geschlossenen Rohr Goettig; Chemische Berichte; vol. 9; (1876); p. 1474 View in Reaxys
O–
I
2
K+
O
O–
O
O
O
Rx-ID: 631931 View in Reaxys 11/11 Yield
Conditions & References Goettig; Chemische Berichte; vol. 9; p. 1475 View in Reaxys T= 100 °C Foelsing; Chemische Berichte; vol. 17; p. 484 View in Reaxys
Copyright © 2018 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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