Query Query
Date
14 reactions in Reaxys
2016-05-03 18h:55m:56s (EST)
O
OH
1. Query HO
Results
OH
O
O
Search as: As drawn, No salts, No mixtures
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OH
O
O
O
O S
HO
OH
O
O O
Rx-ID: 753271 View in Reaxys 1/14 Yield 92 %
Conditions & References With potassium carbonate in acetone Jieping, Zhu; Qian, Wang; Yulin, Li; Journal of the Chemical Society, Chemical Communications; nb. 23; (1988); p. 1549 - 1550 View in Reaxys
92 %
With potassium carbonate in acetone, Time= 48h, Reflux Sagrera, Gabriel; Seoane, Gustavo; Synthesis; nb. 16; (2010); p. 2776 - 2786; Art.No: M06509SS View in Reaxys
91 %
With potassium carbonate in acetone, Time= 0.0666667h, Heating, Microwave irradiation Tsukayama, Masao; Kusunoki, Eiji; Hossain, Mohammad M.; Kawamura, Yasuhiko; Hayashi, Shinji; Heterocycles; vol. 71; nb. 7; (2007); p. 1589 - 1600 View in Reaxys
90 %
With N-hexadecyl-N,N,N-trimethylammonium bromide in sodium hydroxide, chloroform, Ambient temperature Nath, Swadhin; Bhattacharyya, Anjan; Sengupta, P. K.; Journal of the Indian Chemical Society; vol. 60; (1983); p. 801 - 802 View in Reaxys
90.2 %
With potassium carbonate in acetone, Time= 24h, T= 20 - 60 °C Yang, Jincheng; Yang, Tao; Luo, Youfu; He, Jun; Shi, Jianyou; Peng, Aihua; Letters in Organic Chemistry; vol. 8; nb. 4; (2011); p. 258 - 263 View in Reaxys
80 %
With potassium carbonate in acetone, Time= 24h, Heating Asolkar, Ratnakar N.; Kamat, Vijayendra P.; Kirtany, Janardan K.; Journal of Chemical Research - Part S; nb. 12; (2001); p. 549 - 550 View in Reaxys
80 %
With potassium carbonate in acetone, Time= 8h, T= 60 °C Li, Chia-Ying; Lin, Chun-Hua; Wu, Chia-Che; Lee, Kuo-Hsiung; Wu, Tian-Shung; Journal of Agricultural and Food Chemistry; vol. 52; nb. 12; (2004); p. 3721 - 3725 View in Reaxys
80 %
With potassium carbonate in acetone, T= 20 °C Catalan, Luis Espinoza; Maturana, Evelyn Baeza; Marin, Karen Catalan; Olivares, Mauricio Osorio; Altamirano, Hector Carrasco; Fritis, Mauricio Cuellar; Garcia, Joan Villena; Molecules; vol. 15; nb. 9; (2010); p. 6502 6511 View in Reaxys
80 %
Procedure for the Synthesis of 1,3,5-trimethoxybenzene2 Benzene-1,3,5-triol (0.126 g, 1.0 mmol) was dissolved inacetone (20 mL), K2CO3 (0.55 g, 4 mmol) was added, stirredfor a while, and then dimethyl sulfate (0.2 mL, 2 mmol) wasadded dropwise at room temperature for 6 h. The resultingmixture was poured into water when the starting materialdisappeared, extracted with ethyl acetate, the organic phasewas separated and dried over anhydrous MgSO4. The organicphase was concentrated under reduced pressure to give awhite solid 2.Yield: 80percent; 1H NMR (CDCl3, 400 MHz, ppm): 6.08 (s,3H), 3.77 (s, 9H). With potassium carbonate in acetone, Time= 6h, T= 20 °C Hu, Liming; Li, Zhipeng; Wang, Zhanyang; Liu, Gengxin; He, Xianzhuo; Wang, Xiaoli; Zeng, Chengchu; Medicinal Chemistry; vol. 11; nb. 2; (2015); p. 180 - 187
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 73 %
With sodium hydroxide in acetone, 1.) RT, 1 h, 2.) reflux, 30 min Bell, Kevin H.; Australian Journal of Chemistry; vol. 38; nb. 8; (1985); p. 1209 - 1221 View in Reaxys
47 %
With potassium carbonate in acetone, Inert atmosphere Sum, Tze Han; Sum, Tze Jing; Stokes, Jamie E.; Galloway, Warren R.J.D.; Spring, David R.; Tetrahedron; vol. 71; nb. 26-27; (2015); p. 4557 - 4564 View in Reaxys With methanol, man fuegt tropfenweise Kalilauge hinzu Herzig; Wenzel; Monatshefte fuer Chemie; vol. 27; (1906); p. 785 View in Reaxys With acetone Bredereck et al.; Chemische Berichte; vol. 86; (1953); p. 1085,1093 View in Reaxys Clark-Lewis; Australian Journal of Chemistry; vol. 10; (1957); p. 505 View in Reaxys Fischer, Alfred; Henderson, George Narayanan; Canadian Journal of Chemistry; vol. 61; (1983); p. 1045 - 1052 View in Reaxys With potassium carbonate Arevalo, F.; Castedo, L.; Fernandez, B. R.; Mourino, A.; Sarandeses, L.; Chemistry Letters; nb. 5; (1988); p. 745 - 748 View in Reaxys in acetone, Time= 4h, Heating Chassaing, Stefan; Isorez-Mahler, Graldine; Kueny-Stotz, Marie; Brouillard, Raymond; Tetrahedron; vol. 71; nb. 20; (2015); p. 3066 - 3078 View in Reaxys
OH
O
O
HO
OH
O
O O O
Rx-ID: 39878683 View in Reaxys 2/14 Yield 14.6%
Conditions & References 5.2 : Example 5: Methylatwn of 1,3,5-benzenetr l with dimethylcarhonate and CG under m icro wa ve conditions Example 5: Methylatwn of 1,3,5-benzenetr l with dimethylcarhonate and CG under m icro wa ve conditions Procedure: A solution of 1 ,3,5-trihydroxybenzene (1.074 mmol), CssCO (.1.074 ιηιηο), DMC' (2 ml), mesitylene std. (100 μ}3 and CHjC (5 niL) were heated in a 30 mL air tight glass vessel in an Anton Paar Monowave 300 microwave synthesis reactor at 160 °C with a stir rate of 600 rpro. The pressure of the reaction mixture increased from 0- 1 1.4 bar over the duratio of 120 minutes. After 120 minutes, the reaction was cooled to room temperature, pressure released and heated further 240 minutes respectively, and the reaction mixtures were analysed by GC-FID and GC-MS. Results are shown in Table 5. * percent yield corresponds to ^meth lated product In. the experiments in Table 5, the starting to-hydroxy compound is not observed in the GC-FID results. This could be because the tri-rnethoxy product is the only compound formed or because the mono-methoxy-dihydroxy compound does not pass through the GC column. With caesium carbonate in acetonitrile, Time= 4h, T= 160 °C , p= 0 - 8550.86Torr , Microwave irradiation, Time Patent; THE UNIVERSITY OF SYDNEY; MASCHMEYER, Thomas; LOKARE, Kapil, Shyam; MASTERS, Anthony, Frederick; WO2015/51402; (2015); (A1) English View in Reaxys
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OH
O
O
O
O
O
OH
HO HO
OH
O
OH
OH
Rx-ID: 9865999 View in Reaxys 3/14 Yield
Conditions & References
47 %
With sulfuric acid, Time= 24h, Heating Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.; Journal of Medicinal Chemistry; vol. 48; nb. 7; (2005); p. 2407 - 2419 View in Reaxys
2H
OH 2H
2H
HO
O S
2H
OH
O2H
O
O
2H
2H
O
O
2H
2H
2H
2H 2H
2H
O 2H
2H
Rx-ID: 10026325 View in Reaxys 4/14 Yield
Conditions & References With potassium carbonate in acetone, Time= 3h, Heating Lee, Peter J.; Chen, Weibin; Gebler, John C.; Analytical Chemistry; vol. 76; nb. 16; (2004); p. 4888 - 4893 View in Reaxys
OH
HO
O
OH
O
O
Rx-ID: 22241805 View in Reaxys 5/14 Yield
Conditions & References Reaction Steps: 2 1: pyridine 2: methanol; aqueous KOH-solution With pyridine, methanol, potassium hydroxide Freudenberg; Justus Liebigs Annalen der Chemie; vol. 433; (1923); p. 236 View in Reaxys Reaction Steps: 2 1: NaOH-solution 2: platinum chips / 300 - 320 °C With sodium hydroxide, platinum Freudenberg; Chemische Berichte; vol. 53; (1920); p. 1427; Chemische Berichte; vol. 55; (1922); p. 1941 View in Reaxys
OH
Cl
O
O
H HO
OH
O
Rx-ID: 6475326 View in Reaxys 6/14 Yield
Conditions & References folgende Methylierung mit Dimethylsulfat und Kalilauge Freudenberg; Chemische Berichte; vol. 53; (1920); p. 1427; Chemische Berichte; vol. 55; (1922); p. 1941 View in Reaxys
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OH
N
O
N
O
O HO
OH
O
Rx-ID: 4778 View in Reaxys 7/14 Yield
Conditions & References Nierenstein; Chem. Zentralbl.; vol. 77; nb. I; (1906); p. 553 View in Reaxys
OH
N
O
O
N HO
OH
O
Rx-ID: 4779 View in Reaxys 8/14 Yield
Conditions & References With diethyl ether Nierenstein; Chem. Zentralbl.; vol. 77; nb. I; (1906); p. 553 View in Reaxys Herzig; Wenzel; Monatshefte fuer Chemie; vol. 27; (1906); p. 785 View in Reaxys
OH
O –O
HO HO
Na +
O
I
OH
O
Rx-ID: 840000 View in Reaxys 9/14 Yield
Conditions & References Herzig; Wenzel; Monatshefte fuer Chemie; vol. 27; (1906); p. 785 View in Reaxys
OH
O
O
I HO
OH
O
Rx-ID: 840189 View in Reaxys 10/14 Yield
Conditions & References With methanol, man troepfelt methylalkoholische Natriummethylatloesung hinzu Herzig; Wenzel; Monatshefte fuer Chemie; vol. 27; (1906); p. 785 View in Reaxys OH
O HO
O
KOH-solution
S HO
O
O
OH
O
OH
O
O
O
O
O
OH
OH
Rx-ID: 6567648 View in Reaxys 11/14 Yield
Conditions & References Herzig; Wenzel; Monatshefte fuer Chemie; vol. 27; (1906); p. 785 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.
5/6
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OH
O
O
HO HO
OH
O
Rx-ID: 51811 View in Reaxys 12/14 Yield
Conditions & References With sulfuric acid, man setzt Wasser hinzu schuettelt mit Aether aus, versetzt den Rueckstand mit Kalilauge und portionsweise mit Dimethylsulfat und treibt nach beendigter Reaktion mit Wasserdampf ueber Mannich; Archiv der Pharmazie (Weinheim, Germany); vol. 242; (1904); p. 501 View in Reaxys
OH
Cl
H
O
O
HO HO
OH
O
Rx-ID: 6475327 View in Reaxys 13/14 Yield
Conditions & References Herzig; Kaserer; Monatshefte fuer Chemie; vol. 21; (1900); p. 876 View in Reaxys
OH
O
O
phloroglucinolmono and -dimethyl ether
HO HO
OH
O
Rx-ID: 6730696 View in Reaxys 14/14 Yield
Conditions & References With hydrogenchloride Herzig; Kaserer; Monatshefte fuer Chemie; vol. 21; (1900); p. 876 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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