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Date
36 reactions in Reaxys
2016-06-06 00h:30m:38s (EST)
OH
O
1. Query
OH
Search as: As drawn
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1/11
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HO
HO
OH
Br O
O
Rx-ID: 29375242 View in Reaxys 1/36 Yield
Conditions & References
65 %
General procedure for the synthesis of phenol: General procedure: An oven-dried Schlenk tube was charged with CuI (4 mg, 0.02 mmol), aryl bromide (1 mmol), L10 (9 mg, 0.04 mmol) and CsOH (504 mg, 3 mmol) (or KOH (168 mg, 3 mmol)). The tube was evacuated and backfilled with argon, and then DMSO (1 mL), t-BuOH (1 mL) and H2O (0.1 mL) were added. The reaction mixture was stirred at indicated temperatures until the starting material was completely converted (monitored by TLC). The cooled solution mixture was acidified to pH = 1-2 with 2 N HCl, and then extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified with flash chromatography to give the corresponding phenol. Stage 1: With copper(l) iodide, CsOH, C8H6BrN3 in water, dimethyl sulfoxide, tert-butyl alcohol, Time= 36h, T= 120 °C , Inert atmosphere Stage 2: With hydrogenchloride in water, dimethyl sulfoxide, tert-butyl alcohol, pH= 1 - 2, Inert atmosphere Jia, Jianhuan; Jiang, Chenglin; Zhang, Xiaojing; Jiang, Yongwen; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 43; (2011); p. 5593 - 5595 View in Reaxys
62 %
With copper(I) oxide, Pyridine-2-carbaldehyde oxime, CsOH, tetrabutylammomium bromide in water, Time= 48h, T= 110 °C , Inert atmosphere Yang, Daoshan; Fu, Hua; Chemistry - A European Journal; vol. 16; nb. 8; (2010); p. 2366 - 2370 View in Reaxys
O
HO
O
OH
O
O
Rx-ID: 1254931 View in Reaxys 2/36 Yield
Conditions & References
97 %
With boron tribromide in dichloromethane, Time= 1h, T= -78 - 0 °C Li, Chaomin; Johnson, Richard P.; Porco Jr., John A.; Journal of the American Chemical Society; vol. 125; nb. 17; (2003); p. 5095 - 5106 View in Reaxys With boron triiodide Lansinger,J.M.; Ronald,R.C.; Synthetic Communications; vol. 9; (1979); p. 341 - 349 View in Reaxys With boron tribromide in chloroform, Condensation, demethylation Illescas, Beatriz M.; Martin, Nazario; Journal of Organic Chemistry; vol. 65; nb. 19; (2000); p. 5986 - 5995 View in Reaxys O HO
O Si
O Si
OH O
Rx-ID: 2576197 View in Reaxys 3/36 Yield 87 %
Conditions & References With potassium fluoride, hydrogen bromide in N,N-dimethyl-formamide, Time= 2h, T= 25 °C Sinhababu, Achintya K.; Kawase, Masami; Borchardt, Ronald T.; Synthesis; nb. 9; (1988); p. 710 - 712
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2/11
2016-06-06 00:38:44
View in Reaxys
HO
N
O
OH
OH O
Rx-ID: 8605311 View in Reaxys 4/36 Yield
Conditions & References
72 %
With ozone in methanol, Time= 0.0833333h, T= -78 °C , Oxidation Cho, Young Jin; Lee, Seung Hwan; Bae, Jong Woo; Pyun, Hyung-Jung; Yoon, Cheol Min; Tetrahedron Letters; vol. 41; nb. 20; (2000); p. 3915 - 3917 View in Reaxys O
O
O
HO
O O
O
HO
O
OH O
OH
Rx-ID: 33953064 View in Reaxys 5/36 Yield
Conditions & References
94 %
Stage 1: With potassium phosphate in ethanol, Time= 0.833333h, T= 20 °C Stage 2: With ammonium chloride in ethanol Undale, Kedar A.; Gaikwad, Dipak S.; Shaikh, Tarannum S.; Desai, Uday V.; Pore, Dattaprasad M.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 51; nb. 7; (2012); p. 1039 - 1042 View in Reaxys
HO
HO
OH
O O
O
Rx-ID: 32784845 View in Reaxys 6/36 Yield
Conditions & References
70 %
With 1-butylpyridinium bromide, T= 100 °C , Microwave irradiation, Neat (no solvent) Passiniemi, Mikko; Myllymaeki, Mikko J.; Vuokko, Juha; Koskinen, Ari M.P.; Letters in Organic Chemistry; vol. 8; nb. 1; (2011); p. 48 - 52 View in Reaxys Reaction Steps: 2 1: sodium acetate; acetic acid; bromine / 1 h / 20 °C 2: boron tribromide / dichloromethane / 12 h / -78 - 20 °C / |Inert atmosphere With bromine, sodium acetate, boron tribromide, acetic acid in dichloromethane Fouqu, Amlie; Delalande, Olivier; Jean, Mickael; Castellano, Rmy; Josselin, Emmanuelle; Malleter, Marine; Shoji, Kenji F.; Hung, Mac Dinh; Rampanarivo, Hariniaina; Collette, Yves; Van De Weghe, Pierre; Legembre, Patrick; Journal of Medicinal Chemistry; vol. 58; nb. 16; (2015); p. 6559 - 6573 View in Reaxys
Cl
HO
Cl HO
OH OH
Cl O
Rx-ID: 718211 View in Reaxys 7/36 Yield 32.6 %
Conditions & References With sodium hydroxide in water, Time= 8h, Reflux, Inert atmosphere Li, Li-Jun; Tian, Chao; Wang, Zheng; Wang, Guang-Yuan; Wang, Lian-Zeng; Du, Jian-Long; Journal of Chemical Research; vol. 36; nb. 2; (2012); p. 85 - 89
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3/11
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View in Reaxys 32.6 %
With sodium hydroxide in water, Time= 8h, Reflux Li, Lijun; Tian, Chao; Wang, Cheng; Wang, Guangyuan; Wang, Lianzeng; Du, Jianlong; E-Journal of Chemistry; vol. 9; nb. 3; (2012); p. 1422 - 1430 View in Reaxys With sodium hydroxide Tiemann; Mueller; Chemische Berichte; vol. 14; (1881); p. 1986 View in Reaxys With potassium hydroxide Neubauer; Flatow; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 52; (1907); p. 392 View in Reaxys
HO
HO O
HO
H
O HO
O O
O H
OH
HO
O
OH
HO
O
OH
OH
Rx-ID: 28408643 View in Reaxys 8/36 Yield
Conditions & References
97 %
With water in methanol, Irradiation, Quantum yield Kostikov, Alexey P.; Popik, Vladimir V.; Organic Letters; vol. 10; nb. 22; (2008); p. 5277 - 5280 View in Reaxys Br HO
HO
OH
O O
O
Rx-ID: 41128349 View in Reaxys 9/36 Yield
Conditions & References With boron tribromide in dichloromethane, Time= 12h, T= -78 - 20 °C , Inert atmosphere Fouqu, Amlie; Delalande, Olivier; Jean, Mickael; Castellano, Rmy; Josselin, Emmanuelle; Malleter, Marine; Shoji, Kenji F.; Hung, Mac Dinh; Rampanarivo, Hariniaina; Collette, Yves; Van De Weghe, Pierre; Legembre, Patrick; Journal of Medicinal Chemistry; vol. 58; nb. 16; (2015); p. 6559 - 6573 View in Reaxys
HO
O O
OH
O
O
Rx-ID: 1716798 View in Reaxys 10/36 Yield
Conditions & References
53 %
in xylene, Heating Balci, Metin; Suetbeyaz, Yasar; Tetrahedron Letters; vol. 24; nb. 3; (1983); p. 311 - 314 View in Reaxys O
HO
HO
HO
O
OH
OH
O O
O
Rx-ID: 8931832 View in Reaxys 11/36
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.
4/11
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Yield
Conditions & References With 9,10-dihydro-anthracene, T= 526.84 °C , p= 5E-05Torr , Activation energy, Further Variations: Temperatures Pratt; De Heer; Mulder; Ingold; Journal of the American Chemical Society; vol. 123; nb. 23; (2001); p. 5518 - 5526 View in Reaxys
HO
HO
HO
OH
OH
OH O
OH
Rx-ID: 11238648 View in Reaxys 12/36 Yield
Conditions & References With methyl-p-benzoquinone in methanol, Irradiation Kostikov, Alexey P.; Popik, Vladimir V.; Journal of Organic Chemistry; vol. 72; nb. 24; (2007); p. 9190 - 9194 View in Reaxys
HO
HO
OH
O
O
Rx-ID: 609275 View in Reaxys 13/36 Yield
Conditions & References With sodium hydroxide, potassium peroxomonosulphate, Spalten des entstehenden Gentisinaldehydmonoschwefelsaeureesters durch Erhitzen mit rauchender Salzsaeure bei 70grad Neubauer; Flatow; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 52; (1907); p. 392 View in Reaxys With sodium hydroxide, (NH4)2S2O8, und Erwaermen des Reaktionsprodukts mit konz.wss.Salzsaeure auf 75grad Rodriguez Velasco; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 32; (1934); p. 345,356 View in Reaxys
2.4 g
With dipotassium peroxodisulfate Iinuma; Iwashima; Matsuura; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 12; (1984); p. 4935 - 4941 View in Reaxys
O
HO
OH
OH O
Rx-ID: 660402 View in Reaxys 14/36 Yield
Conditions & References With sodium hydroxide, potassium peroxomonosulphate, T= 30 - 35 °C , und Erhitzen des Reaktionsprodukts mit konz.Salzsaeure auf 70grad Hodgson; Beard; Journal of the Chemical Society; (1927); p. 2340 View in Reaxys
H
HO
O
OH
OH
O O
Rx-ID: 2690841 View in Reaxys 15/36 Yield 10 %, 8 %
Conditions & References With dihydrogen peroxide, hydrogen fluoride, SbF5, Time= 0.5h, T= -20 °C , Mechanism, Product distribution
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5/11
2016-06-06 00:38:44
Gesson, Jean-Pierre; Jacquesy, Jean-Claude; Jouannetaud, Marie-Paule; Morellet, Guy; Tetrahedron Letters; vol. 24; nb. 30; (1983); p. 3095 - 3098 View in Reaxys 8 %, 10 %
With dihydrogen peroxide, hydrogen fluoride, SbF5, Time= 0.5h, T= -20 °C Gesson, Jean-Pierre; Jacquesy, Jean-Claude; Jouannetaud, Marie-Paule; Morellet, Guy; Tetrahedron Letters; vol. 24; nb. 30; (1983); p. 3095 - 3098 View in Reaxys
10 %, 8 %
With dihydrogen peroxide, hydrogen fluoride, SbF5, Time= 0.5h, T= -20 °C Gesson, Jean-Pierre; Jacquesy, Jean-Claude; Jouannetaud, Marie-Paule; Morellet, Guy; Tetrahedron Letters; vol. 24; nb. 30; (1983); p. 3095 - 3098 View in Reaxys
HO
O
O
O
O
OH O
Rx-ID: 20713573 View in Reaxys 16/36 Yield
Conditions & References Reaction Steps: 2 1: 1) t-BuLi; 2) MgBr2-etherate / 1) petroleum ether, 0 deg C; 2) 40 deg C 42 h 2: treatment with acid With tert.-butyl lithium, magnesium bromide Ronald, Robert C.; Winkle, Mark R.; Tetrahedron; vol. 39; nb. 12; (1983); p. 2031 - 2042 View in Reaxys Reaction Steps: 2 1: 1) t-BuLi; 2) MgBr2-etherate / 1) petroleum ether, 0 deg C; 2) 40 deg C 42 h 2: treatment with acid With tert.-butyl lithium, magnesium bromide Ronald, Robert C.; Winkle, Mark R.; Tetrahedron; vol. 39; nb. 12; (1983); p. 2031 - 2042 View in Reaxys Reaction Steps: 2 1: 1) t-BuLi; 2) MgBr2-etherate / 1) petroleum ether, 0 deg C; 2) 40 deg C 42 h 2: treatment with acid With tert.-butyl lithium, magnesium bromide Ronald, Robert C.; Winkle, Mark R.; Tetrahedron; vol. 39; nb. 12; (1983); p. 2031 - 2042 View in Reaxys
HO
O
HO
HO
OH
OH
OH
O
Rx-ID: 11238649 View in Reaxys 17/36 Yield
Conditions & References in methanol, Irradiation Kostikov, Alexey P.; Popik, Vladimir V.; Journal of Organic Chemistry; vol. 72; nb. 24; (2007); p. 9190 - 9194 View in Reaxys
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6/11
2016-06-06 00:38:44
O HO
O OH O
O
Rx-ID: 4308943 View in Reaxys 18/36 Yield
Conditions & References in benzene, Irradiation Bruce,J.M.; Creed,D.; Journal of the Chemical Society [Section] C: Organic; (1970); p. 649 - 653 View in Reaxys O
HO
HO
O
O
O OH
HO
HO
HO
O
Rx-ID: 5322019 View in Reaxys 19/36 Yield
Conditions & References in water, Formation of xenobiotics, simulated solar irradiation, Oxidation, Further byproducts given Mallakin, Ali; George Dixon; Greenberg, Bruce M.; Chemosphere; vol. 40; nb. 12; (2000); p. 1435 - 1441 View in Reaxys
OH
O
HO
O
HO
OH
OH O
OH
Rx-ID: 28408640 View in Reaxys 20/36 Yield
Conditions & References With water in methanol, Irradiation, Quantum yield Kostikov, Alexey P.; Popik, Vladimir V.; Organic Letters; vol. 10; nb. 22; (2008); p. 5277 - 5280 View in Reaxys
HO
HO
HO
H O
O
OH
O
OH
O
O
O
O
OH
O HO
Rx-ID: 28323917 View in Reaxys 21/36 Yield
Conditions & References With oxygen, Titanium(IV) oxide in water, Irradiation Augugliaro, Vincenzo; Caronna, Tullio; Loddo, Vittorio; Marci, Giuseppe; Palmisano, Giovanni; Palmisano, Leonardo; Yurdakal, Sedat; Chemistry - A European Journal; vol. 14; nb. 15; (2008); p. 4640 - 4646 View in Reaxys
HO
O
HO
OH OH O
Rx-ID: 718155 View in Reaxys 22/36 Yield
Conditions & References in Gegenwart einer aromatischen Hydroxylaminsulfonsaeure und Spaltung des Kondensationsproduktes Patent; Geigy and Co.; DE105798
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7/11
2016-06-06 00:38:44
View in Reaxys in Gegenwart einer aromatischen Hydroxylaminsulfonsaeure und Zersetzung des Reaktionsproduktes Patent; Geigy and Co.; DE105798 View in Reaxys With tributyl-amine, tin(IV) chloride, 1.) toluene, room temperature, 20 min, 2.) 100 deg C, 8 h, Yield given. Multistep reaction Casiraghi, Giovanni; Casnati, Giuseppe; Puglia, Giuseppe; Sartori, Giovanni; Terenghi, Giuliana; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1862 1865 View in Reaxys
O HO
O OH
O
O
O
O
O
Rx-ID: 2846934 View in Reaxys 23/36 Yield
Conditions & References treatment with acid Ronald, Robert C.; Winkle, Mark R.; Tetrahedron; vol. 39; nb. 12; (1983); p. 2031 - 2042 View in Reaxys
O HO
O O
O
OH
O O
O
Rx-ID: 2919698 View in Reaxys 24/36 Yield
Conditions & References treatment with acid Ronald, Robert C.; Winkle, Mark R.; Tetrahedron; vol. 39; nb. 12; (1983); p. 2031 - 2042 View in Reaxys
O HO
O O
O
O
O
OH O
Rx-ID: 2932157 View in Reaxys 25/36 Yield
Conditions & References treatment with acid Ronald, Robert C.; Winkle, Mark R.; Tetrahedron; vol. 39; nb. 12; (1983); p. 2031 - 2042 View in Reaxys
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8/11
2016-06-06 00:38:44
O
HO
HO
HO
HO
HO OH
HO
HO
O
O
O
Rx-ID: 11078654 View in Reaxys 26/36 Yield
Conditions & References
57 % Spectr., 4 % Spectr., 4% Spectr., 4 % Spectr.
With biphenyl in acetone, Time= 2h, T= 30 °C , Product distribution, Further Variations: Reagents, Solvents, reaction times Zalomaeva, Olga V.; Sorokin, Alexander B.; New Journal of Chemistry; vol. 30; nb. 12; (2006); p. 1768 - 1773 View in Reaxys
O OH
O
HO
N O
O
potassium persulfate
OH
O
O
Rx-ID: 5802296 View in Reaxys 27/36 Yield
Conditions & References T= 30 - 35 °C , Erhitzen des Reaktionsprodukts mit konz.Salzsaeure auf 70grad Hodgson; Beard; Journal of the Chemical Society; (1927); p. 2340 View in Reaxys
HO
Cl
HO
H OH
O
Cl
O
O
Rx-ID: 6671998 View in Reaxys 28/36 Yield
Conditions & References T= 140 - 150 °C Tiemann; Mueller; Chemische Berichte; vol. 14; (1881); p. 1986 View in Reaxys
Cl
HO
Cl HO
OH
Cl
aqueous NaOH-solution
OH O
Rx-ID: 5802294 View in Reaxys 29/36 Yield
Conditions & References Tiemann; Mueller; Chemische Berichte; vol. 14; (1881); p. 1986 View in Reaxys
Cl
HO
Cl HO
OH
Cl
KOH-solution
OH O
Rx-ID: 5802295 View in Reaxys 30/36 Yield
Conditions & References Neubauer; Flatow; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 52; (1907); p. 392 View in Reaxys
O
OH
K2S2O8
diluted aqueous NaOH-solution
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9/11
2016-06-06 00:38:44
HO
OH
O
O
OH OH
Rx-ID: 5809627 View in Reaxys 31/36 Yield
Conditions & References Forrest; Petrow; Journal of the Chemical Society; (1950); p. 2340 View in Reaxys
HO
OH O
Rx-ID: 6520282 View in Reaxys 32/36 Yield
Conditions & References Patent; Montedison S.p.A.; DE2736523; (1978); ; vol. 88; nb. 152247 View in Reaxys Rao et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 2548 View in Reaxys Bruce et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1969); p. 594 View in Reaxys Doppler et al.; Helvetica Chimica Acta; vol. 62; (1979); p. 314,324 View in Reaxys Scott; Beadling; Bioorganic Chemistry; vol. 3; (1974); p. 281,283 View in Reaxys Ulrich et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 2437,2438 View in Reaxys Sekiguchi; Gaucher; Biochemistry; vol. 17; (1978); p. 1785,1786 View in Reaxys A few illustrative examples of preferred aldehydes include ... 3,4-dichlorobenzaldehyde 3,5-dichlorobenzaldehyde 4-(diethylamino)-benzaldehyde 4-[β-(diethylamino)-ethoxy]-benzaldehyde 2,5-dihydroxybenzaldehyde 3,4-dihydroxybenzaldehyde 2,3-dimethoxybenzaldehyde 2,4-dimethoxybenzaldehyde ... Patent; Ethyl Corporation; US4837327; (1989); (A1) English View in Reaxys 13 : 2,5-dihydroxybenzaldehyde EXAMPLE 13 2,5-dihydroxybenzaldehyde The reaction was initially conducted as in Example 1, employing 11.0 g of hydroquinone. At the conclusion of the reaction the mass was filtered, repeatedly washed with water, dried on anhydrous Na2 SO4 and finally evaporated to dryness. Aldehyde was separated from the solid residue by repeatedly crystallizing from a 1:1 benzene:petroleum ether mixture. 6.6 g (yield calculated on the theoretical value=48percent) of a product having a melting point of 99° C. were obtained. The centesimal, infrared and nuclear magnetic resonance analyses agreed with the structure: C7 H6 O3. Patent; Montedison S.p.A.; US4151201; (1979); (A1) English View in Reaxys
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10/11
2016-06-06 00:38:44
HO 2H
OH O
Rx-ID: 7250646 View in Reaxys 33/36 Yield
Conditions & References aus Bestrahlung von 1-(1.4-Benzochinonyl)-1-Deuterio-2-Phenylethanol in Benzol Bruce,J.M. et al.; Journal of the Chemical Society [Section] C: Organic; (1971); p. 2244 - 2252 View in Reaxys Hydrochinon 9, Photorkt.m.CDCl3 Hirao et al.; Tetrahedron; vol. 30; (1974); p. 2301,2305 View in Reaxys 2H
HO 2H
2H
O 2H
OH
Rx-ID: 7397206 View in Reaxys 34/36 Yield
Conditions & References <2,3,5,6-2H>-Hydrochinon (?), NaOH, D2O Scott et al.; Bioorganic Chemistry; vol. 2; (1973); p. 124,136 View in Reaxys B. unklar Scott et al.; Bioorganic Chemistry; vol. 2; (1973); p. 124,136 View in Reaxys OH 2H
O 2H
2H
OH
Rx-ID: 7395056 View in Reaxys 35/36 Yield
Conditions & References Gentisaldehyd, D2O Scott et al.; Bioorganic Chemistry; vol. 2; (1973); p. 124,136 View in Reaxys
HO H 14C
OH
O
Rx-ID: 7686400 View in Reaxys 36/36 Yield
Conditions & References 2-Brom-p-hydrochinon, 1. Cu14CN, 2. Raney-Nickel, NaH2PO2, Reduktion Billek et al.; Journal of Labelled Compounds; vol. 5; (1969); p. 3,7 View in Reaxys
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11/11
2016-06-06 00:38:44