2-'ALK'benzene-1,4-diol by Asch

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Reactions (322)

Yield

Substances (32)

Citations (235)

Conditions

References

199

Synthesize Find similar Multi-step reaction with 3 steps 1: AlCl3 / nitrobenzene 2: aq. HBr / acetic acid 3: aq. N2H4, KOH, triethylene glycol / Heating View Scheme

200

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Rx-ID: 22793814 Find similar reactions

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

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Rx-ID: 22809224 Find similar reactions

Multi-step reaction with 3 steps 1: AlCl3 / nitrobenzene 2: aq. HBr / acetic acid 3: aq. N2H4, KOH, triethylene glycol / Heating View Scheme

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

201

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Rx-ID: 23983743 Find similar reactions

Mrksich, Milan; Hodneland, Christian

Patent: US2003/119054 A1, 2003 ;

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Title/Abstract Full Text Show Details

12:Synthesis of Soluble NTA-quinone Conjugate

Example 12 Synthesis of Soluble NTA-quinone Conjugate n-Pentylhydroquinone 21. To the solution of 2.4 g (11.5 mmol) of n-Pentyldimethoxybenzene 1 in CH2Cl2 at -78° C., 5.4 ml (5 eq) of BBr3 was added dropwise. After warming to room temperature, the reaction mixture was stirred for 4 hr. The BBr3 was quenched with ethyl ether at -78° C., and then with water at room temperature. Extraction with CH2Cl2 and silicagel chromatography (hexane:EA=2:1) gave 2.07 g (quant.) of 21 as a white solid.

202

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Multi-step reaction with 2 steps 1.1: tetrahydrofuran; pentane / 1.33 h / 0 - 20 °C / |Inert atmosphere 1.2: 15 h / 0 - 20 °C / |Inert atmosphere 2.1: boron tribromide / dichloromethane / 4 h / -78 - 20 °C / |Inert atmosphere View Scheme

Rx-ID: 42005044 Find similar reactions

The University of Chicago; MRKSICH, Milan; HODNELAND, Christian

Patent: US2015/369816 A1, 2015 ; Title/Abstract Full Text Show Details

203

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Rx-ID: 42005050 Find similar reactions

The University of Chicago; MRKSICH, Milan; HODNELAND, Christian

Patent: US2015/369816 A1, 2015 ; Title/Abstract Full Text Show Details

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204

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With water

UV-irradiation;

Tchaikovskaya, Olga N.; Karetnikova, Elena A.; Sokolova, Irina V.; Mayer, Georgy V.; Shvornev, Dmitry A.

Journal of Photochemistry and Photobiology A: Chemistry, 2012 , vol. 228, # 1 p. 8 - 14 Title/Abstract Full Text View citing articles Show Details

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205

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B: 64 % Turnov.

With triethylamine in ethanol

2 h; Irradiation;

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Pandey, Bipin; Dalvi, Pramod V.

Angewandte Chemie, 1993 , vol. 105, # 11 p. 1724 - 1726 Title/Abstract Full Text Show Details

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206

Rx-ID: 8122145 Find similar reactions

With aluminum tri-bromide; benzene

Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

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207

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A: 87.7% B: 2.6% C: 9.7%

With isopropyl alcohol; Candida antarctica lipase B; immobilized in di-isopropyl ether

T=45°C; 1 h; Title compound not separated from byproducts.;

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

208

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With sodium hydroxide; dipotassium peroxodisulfate

Erwaermen des Reaktionsprodukts mit konz. wss. HCl auf 70grad;

Rx-ID: 289728 Find similar reactions

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

209

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Rx-ID: 466124 Find similar reactions

With aluminium trichloride; toluene

Brockmann; Mueller

Justus Liebigs Annalen der Chemie, 1939 , vol. 540, p. 51,62 Full Text Show Details

210

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Rx-ID: 466126 Find similar reactions

With hydrogen bromide

Lowe et al.

Journal of the Chemical Society, 1951 , p. 3286,3291 Full Text Show Details

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211

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With hydrogen fluoride

anfangs bei 5grad bis 10grad;

Calcott; Tinker; Weinmayr

Journal of the American Chemical Society, 1939 , vol. 61, p. 1010,1014 Full Text Show Details

Bogoljubsski

Zhurnal Obshchei Khimii, 1962 , vol. 32, p. 869,870 J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 862,863 Full Text Show Details

With hydrogenchloride; zinc(II) chloride

Bogoljubsski

T=96 - 98°C;

Zhurnal Obshchei Khimii, 1962 , vol. 32, p. 869,870 J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 862,863 Full Text Show Details

212

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Rx-ID: 4124182 Find similar reactions

With hydrogen; copper (II) chromite in ethanol

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

213

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Rx-ID: 4686155 Find similar reactions

86%

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With lithium chloride in various solvent(s) T=160 - 170°C; 1 h;

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

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214

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T=5 - 20°C;

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Calcott; Tinker; Weinmayr

Journal of the American Chemical Society, 1939 , vol. 61, p. 1010,1014 Full Text Show Details

Bogoljubsski

Zhurnal Obshchei Khimii, 1962 , vol. 32, p. 869,870 J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 862,863 Full Text Show Details

215

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Rx-ID: 7185804 Find similar reactions

Benzochinon-(1,4), Ae., Trihexylboran, sd. Ae., N2, ca. 1 h;

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

(yield)ca. 98percent;

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

216

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T=70°C; Erwaermen des Reaktionsprodukts mit konz. wss. HCl;

Rx-ID: 7185805 Find similar reactions

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

217

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With hydrogenchloride; amalgamated zinc

Rx-ID: 8121895 Find similar reactions

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

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218

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Rx-ID: 10442064 Find similar reactions

A: 65% B: 21%

Stage #1: 1,1,2,2-tetramethylethylene With dimethylsulfide borane complex in dimethylsulfide

T=0°C; 2.5 h; Inert atmosphere; Stage #2: With 2-benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol in dimethylsulfide; dichloromethane

T=0 - 20°C; Inert atmosphere; Stage #3: p-benozquinone With N,N'-dimethyl-N,N'-propyleneurea in dimethylsulfide; dichloromethane

T=20°C; 2 h; Inert atmosphere;

Luethy, Monique; Darmency, Vincent; Renaud, Philippe

European Journal of Organic Chemistry, 2011 , # 3 p. 547 - 552 Title/Abstract Full Text View citing articles Show Details

A: 60% B: 16%

Stage #1: 1,1,2,2-tetramethylethylene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole in dichloromethane

5 h; Heating; Stage #2: p-benozquinone With N,N'-dimethyl-N,N'-propyleneurea; water in dichloromethane

T=25°C; 2 h;

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

219

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220

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Multi-step reaction with 2 steps 1: N2H4+H2O; ethanol / Erhitzen des Reaktionsprodukts mit KOH auf 170grad 2: aqueous HBr View Scheme

Rx-ID: 22100071 Find similar reactions

Lowe et al.

Journal of the Chemical Society, 1951 , p. 3286,3291 Full Text Show Details

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Rx-ID: 22107946 Find similar reactions

Multi-step reaction with 3 steps 1: AlCl3

2: N2H4+H2O; ethanol / Erhitzen des Reaktionsprodukts mit KOH auf 170grad 3: aqueous HBr View Scheme

Lowe et al.

Journal of the Chemical Society, 1951 , p. 3286,3291 Full Text Show Details

221

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Rx-ID: 22112264 Find similar reactions

Multi-step reaction with 3 steps 1: AlCl3

2: N2H4+H2O; ethanol / Erhitzen des Reaktionsprodukts mit KOH auf 170grad 3: aqueous HBr View Scheme

Lowe et al.

Journal of the Chemical Society, 1951 , p. 3286,3291 Full Text Show Details

222

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223

Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

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Rx-ID: 22407344 Find similar reactions

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

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Rx-ID: 22413591 Find similar reactions

Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

224

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Rx-ID: 24801075 Find similar reactions

59%

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Stage #1: in diethyl ether

T=20°C; Stage #2: With water in diethyl ether

SAN DIEGO STATE UNIVERSITY FOUNDATION

Patent: WO2006/102007 A2, 2006 ; Location in patent: Page/Page column 17-18 ;

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Title/Abstract Full Text Show Details

Example 1; Preparation of l-Hexyl-hydroquinone from i?-l-Hexyldiphenviborane; [0049] A solution of 5-1-hexyldiρhenylborane (7.1 mmol, 1.78 g) in 10 mL of diethyl ether was slowly added to a solution of p-benzoquinone (7.4 mmol, 0.80 g) in 10 mL of diethyl ether. The addition was conducted in a room temperature water-bath to prevent the boiling of the solvent with this exothermic reaction. After the addition was complete approximately 2 mL of water was added to the solution and the mixture was stirred overnight to complete the EPO <DP n="19"/>hydrolysis. The mixture was placed in a separatory runnel along with 5 mL of saturated NaCl solution. The reaction flask was rinsed with an additional 10 mL of diethyl ether, and this was also added to the separatory funnel. The aqueous layer was separated and the solution was washed with an additional 5 mL of NaCl solution. The diethyl ether solution was dried over MgSQ4 and filtered. The solution was placed in an ice-bath, followed by the slow addition of ethanolamine (7.4 mmol, 0.45 mL), which resulted in a heavy precipitate within a couple of minutes. The solvent was removed under vacuum, and the product was extracted with (3 X 10 mL) of hot petroleum ether. The recrystallization of the product from hot petroleum ether produced 0.81 g (59percent yield) of 1-hexyl-hydroquinone as a white solid. 1H NMR (CDCl3): δ 6.64 (m, 2H), 6.55 (dd, J= 8.5, 3 Hz, IH), 4.46 (s, IH), 4.40 (s, IH), 2.55 (t, J= 7.5 Hz, 2H), 1.60 (m, 2H), 1.33 (m, 6H), 0.90 (t, J= 7 Hz, 3H); 13C NMR (CDCl3): 5 149.4, 147.5, 130.1, 116.9, 116.1, 113.3, 31.7, 30.0, 29.6, 29.1, 22.5, 14.0.

225

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Rx-ID: 29520147 Find similar reactions

94%

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Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E.

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036 Title/Abstract Full Text View citing articles Show Details

in tetrahydrofuran; diethyl ether; hexane

T=20°C; Inert atmosphere; regioselective reaction;

226

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Rx-ID: 41627987 Find similar reactions

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Dennig, Alexander; Busto, Eduardo; Kroutil, Wolfgang; Faber, Kurt

ACS Catalysis, 2015 , vol. 5, # 12 p. 7503 - 7506 Title/Abstract Full Text View citing articles Show Details

With glucose dehydrogenase; D-glucose; pyridoxal 5'-phosphate; P450 monooxygenase BM3 variant M2; tyrosine phenol lyase mutant M379V; ammonia; oxygen; NADPH; catalase in aq. phosphate buffer; dimethyl sulfoxide

T=20°C; pH=8; 6 h; Enzymatic reaction; enantioselective reaction;

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227

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Rx-ID: 7443695 Find similar reactions

Eastman Kodak Co.

Patent: US2533203 , 1948 ;

T=95°C;

Full Text Show Details

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228

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Bamberger; Brun

Helvetica Chimica Acta, 1923 , vol. 6, p. 946,947 Helvetica Chimica Acta, 1924 , vol. 7, p. 112,114 Full Text Show Details

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229

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B: 15%

Mehta; Murthy; Reddy

Tetrahedron Letters, 1987 , vol. 28, # 13 p. 1467 - 1468 Title/Abstract Full Text View citing articles Show Details

T=600°C; P=0.8 Torr; flash vacuum pyrolysis;

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230

Synthesize Find similar Rx-ID: 11244699 Find similar reactions

A: 94% B: 6%

With isopropyl alcohol; Candida antarctica lipase B; immobilized in di-isopropyl ether

T=45°C; 1 h; Title compound not separated from byproducts.;

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

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231

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in methanol

T=20°C; 16 h; Irradiationvarious other solvents; Mechanism;

Timpe, Hans-Joachim; Dietrich, Reinhard; Boeckelmann, Juergen; Friedel, Ingrid; Boegel, Horst; Haucke, Guenther

Collection of Czechoslovak Chemical Communications, 1981 , vol. 46, # 1 p. 219 - 239

Title/Abstract Full Text Show Details

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232

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Rx-ID: 6220501 Find similar reactions

Fichter; Ackermann

Helvetica Chimica Acta, 1919 , vol. 2, p. 595 Full Text Show Details

bei der elektrolytischen Oxydation;

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233

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Posner; Lipsky

Justus Liebigs Annalen der Chemie, 1904 , vol. 336, p. 159 Full Text Show Details

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234

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With trifluoroacetic acid

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Haga, Naoki; Endo, Yasuyuki; Kataoka, Ken-Ichiro; Yamaguchi, Kentaro; Shudo, Koichi

1.) 60 deg C, 4 h, 2.) 0 deg C, 2 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Journal of the American Chemical Society, 1992 , vol. 114, # 25 p. 9795 - 9806 Title/Abstract Full Text View citing articles Show Details

With trifluoroacetic acid

1.) 60 deg C, 4 h, 2.) 0 deg C, 2 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

Haga, Naoki; Endo, Yasuyuki; Kataoka, Ken-Ichiro; Yamaguchi, Kentaro; Shudo, Koichi

Journal of the American Chemical Society, 1992 , vol. 114, # 25 p. 9795 - 9806 Title/Abstract Full Text View citing articles Show Details

235

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Rx-ID: 310302 Find similar reactions

With palladium on activated charcoal; acetic acid

Hydrogenation;

Eastman Kodak Co.

Patent: US2728659 , 1953 ;

With ethanol; copper oxide-chromium oxide

T=150 - 160°C; P=172844 Torr; Hydrogenation;

Williams

Journal of Organic Chemistry, 1957 , vol. 22, p. 772 Full Text View citing articles Show Details

With hydrogenchloride; mercury; zinc in ethanol

Ozawa; Momose; Machida; Natori; Yoshihira

Chemical and pharmaceutical bulletin, 1968 , vol. 16, # 5 p. 853 - 862 Title/Abstract Full Text View citing articles Show Details

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Full Text Show Details

Hide Details

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

With hydrogen; copper (II) chromite in ethanol

236

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With hydrogen bromide; acetic acid

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Rx-ID: 365644 Find similar reactions

Quilico; Panizzi; Muganaini

Gazzetta Chimica Italiana, 1949 , vol. 79, p. 89,104 Full Text Show Details

237

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Rx-ID: 718139 Find similar reactions

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With sulfuric acid

T=70 - 80°C;

Roehm and Haas Co.

Patent: US2008337 , 1932 ;

With sulfuric acid; acetic acid

Niederl; Natelson; Beekman

Journal of the American Chemical Society, 1933 , vol. 55, p. 2571,2574 Full Text Show Details

Roehm and Haas Co.

Patent: US2008032 , 1933 ;

Full Text Show Details

Roehm and Haas Co.

Patent: DE666134 , 1933 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 137 Full Text Show Details

Full Text Show Details

Roehm and Haas Co.

Patent: DE657724 , 1934 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 172 Full Text Show Details

Pospisil,J.; Taimr,L.

Collection of Czechoslovak Chemical Communications, 1964 , vol. 29, p. 381 - 389 Full Text View citing articles Show Details

With sulfuric acid in acetic acid

238

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Rx-ID: 4519430 Find similar reactions

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

With boron tribromide in dichloromethane

1) -20 deg C, 1 h; 2) rt, 3 h; Yield given;

239

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Rx-ID: 4785602 Find similar reactions

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Carman, Raymond M.; Kanizaj, Nicholas; Taylor, Richard J.K.

Australian Journal of Chemistry, 1997 , vol. 50, # 5 p. 515 - 516 Title/Abstract Full Text View citing articles Show Details

With Amberlyst IR120 H(1+) in diethyl ether

Ambient temperature;

240

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Rx-ID: 5807899 Find similar reactions

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Roehm and Haas Co.

Patent: US2008337 , 1932 ;

T=20 - 80°C;

Full Text Show Details

Roehm and Haas Co.

Patent: DE666134 , 1933 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 137 Full Text Show Details

241

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Rx-ID: 5807900 Find similar reactions

T=0 - 15°C;

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Niederl; Natelson; Beekman

Journal of the American Chemical Society, 1933 , vol. 55, p. 2571,2574

Full Text Show Details

Roehm and Haas Co.

Patent: US2008032 , 1933 ; Full Text Show Details

Roehm and Haas Co.

Patent: DE657724 , 1934 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 172 Full Text Show Details

242

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Rx-ID: 7190501 Find similar reactions

2-Octanoyl-hydrochinon, H2, Pd-Kohle;

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

Hydrochinon, Octen, H+;

Fuji Photo Film Co.

Patent: JP461464 , 1961 ; Chem.Abstr., 1965 , vol. 63, # 1736c Full Text Show Details

243

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244

Hydrochinon in Eg., H2SO4, Diisobutylen;

Rx-ID: 7195745 Find similar reactions

Pospisil; Taimr

Patent: CS111292 , 1963 ; Chem.Abstr., 1965 , vol. 62, # 6434 Full Text Show Details

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Rx-ID: 10442066 Find similar reactions

72%

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Stage #1: oct-1-ene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole in dichloromethane

5 h; Heating; Stage #2: p-benozquinone With N,N'-dimethyl-N,N'-propyleneurea; water in dichloromethane

T=25°C; 2 h;

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

245

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Rx-ID: 22077272 Find similar reactions

Multi-step reaction with 2 steps 1: BF3

2: palladium/charcoal; acetic acid / Hydrogenation View Scheme

Eastman Kodak Co.

Patent: US2728659 , 1953 ;

Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Full Text Show Details

246

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Multi-step reaction with 2 steps 1: BF3

2: palladium/charcoal; acetic acid / Hydrogenation View Scheme

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Rx-ID: 22109925 Find similar reactions

Eastman Kodak Co.

Patent: US2728659 , 1953 ; Full Text Show Details

247

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Rx-ID: 22407345 Find similar reactions

Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

248

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Rx-ID: 22791544 Find similar reactions

Multi-step reaction with 2 steps 1: aq. HCl / ethanol 2: Zn-Hg, aq. HCl / ethanol View Scheme

Ozawa; Momose; Machida; Natori; Yoshihira

Chemical and pharmaceutical bulletin, 1968 , vol. 16, # 5 p. 853 - 862 Title/Abstract Full Text View citing articles Show Details

249

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Multi-step reaction with 3 steps 1: AlCl3 / CS2

2: aq. HCl / ethanol 3: Zn-Hg, aq. HCl / ethanol View Scheme

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Rx-ID: 22801658 Find similar reactions

Ozawa; Momose; Machida; Natori; Yoshihira

Chemical and pharmaceutical bulletin, 1968 , vol. 16, # 5 p. 853 - 862 Title/Abstract Full Text View citing articles Show Details

250

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Rx-ID: 22809219 Find similar reactions

Multi-step reaction with 3 steps 1: AlCl3 / CS2

2: aq. HCl / ethanol 3: Zn-Hg, aq. HCl / ethanol View Scheme

Ozawa; Momose; Machida; Natori; Yoshihira

Chemical and pharmaceutical bulletin, 1968 , vol. 16, # 5 p. 853 - 862 Title/Abstract Full Text View citing articles Show Details

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251

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Rx-ID: 34649550 Find similar reactions

With 3-(4-sulfobutylamino)propylsilanized MCM-41 in nitrobenzene

T=165°C; Friedel-Crafts Alkylation; 0.166667 h; Microwave irradiationGreen chemistry; chemoselective reaction; Hide Experimental Procedure

Ng, Eng-Poh; Mohd Subari, Siti Norbayu; Marie, Olivier; Mukti, Rino R.; Juan, Joon-Ching

Applied Catalysis A: General, 2013 , vol. 450, p. 34 - 41 Title/Abstract Full Text View citing articles Show Details

2.5. Catalytic experiments

Friedel–Crafts reactions were performed with microwave irradiation assistance by modifying the synthesis condition [30]. Prior to reaction, hydroquinone (Merck, 2.0 mmol), methyl tert-butyl ether (MTBE, Merck, 2.0 mmol) and freshly activated SO3H-MCM-41 catalyst (0.1 g, 100 °C, 3 h) were loaded into a reactor. The reaction was realized in an Anton Paar Synthos 3000 microwave oven under magnetic stirring and 300 W microwave irradiation, while the reaction temperature was monitored by an infrared pyrometer. The samples were withdrawn after the reaction and the liquid phase was separated and analyzed using a gas chromatograph (Hewlett-Packard 5880) equipped with a Carbowax Equity 1 non-polar capillary column. The identity of the product was confirmed by GC–MS (Perkin-Elmer GC-IR 2000 system). A

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252

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Rx-ID: 34649551 Find similar reactions

With 3-(4-sulfobutylamino)propylsilanized MCM-41 in nitrobenzene

Ng, Eng-Poh; Mohd Subari, Siti Norbayu; Marie, Olivier; Mukti, Rino R.; Juan, Joon-Ching

T=150°C; Friedel-Crafts Alkylation; 0.133333 h; Microwave irradiationGreen chemistry; Catalytic behavior; Concentration; chemoselective reaction; Hide Experimental Procedure

Applied Catalysis A: General, 2013 , vol. 450, p. 34 - 41 Title/Abstract Full Text View citing articles Show Details

2.5. Catalytic experiments

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253

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Rx-ID: 36779255 Find similar reactions

D: 48.8%

With porous pillared-zirconium phosphate functionalized with methyl group in anhydrous xylene

T=150°C; 4 h; Autoclave; Reagent/catalyst; Hide Experimental Procedure

Liu, Ke; Wang, Xueyan; Ding, Shengda; Li, Ying; Hua, Weiming; Yue, Yinghong; Gao, Zi

Journal of Molecular Catalysis A: Chemical, 2013 , vol. 380, p. 84 - 89 Title/Abstract Full Text View citing articles Show Details

2.3.1. Alkylation of hydroquinone

Alkylation of hydroquinone with tert-butanol was carried outin an autoclave equipped with a magnetic stirrer. Typically, 0.5 ghydroquinone, 1.0 g tert-butanol, and 0.20 g catalyst were addedto the autoclave, along with 2 g of xylene as a solvent. The reac-tion lasted 4 h under 150C. The products were analyzed witha gas chromatograph equipped with a SE-30 capillary column(30 m × 0.25 mm × 0.3 m) and a flame ionization detector. Thetemperature of the capillary column was set at 180C. The mainproducts were 2-tert-butyl hydroquinone (2-TBHQ), 2,5-di-tert-butyl hydroquinone (2,5-TBHQ), 2,5-di-tert-butyl benzoquinone(2,5-DTBBQ) and tert-butyl phenol ether (TBPE).

With perfluorosulfonicacid functionalized carbon nanotubes (PFSA CNT 0.5) in anhydrous xylene

4 h; Autoclave; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure

Zhang, Mengxiao; Li, Cuican; Hua, Weiming; Yue, Yinghong; Gao, Zi

Chinese Journal of Catalysis, 2014 , vol. 35, # 11 p. 1874 - 1882 Title/Abstract Full Text Show Details

Catalytic testing

Alkylation of hydroquinone was carried out in a stainlesssteel autoclave with a PTFE liner using magnetic stirring. Typically,0.5 g hydroquinone, 1.0 g tert butanol, and 0.2 g catalystwere added in the autoclave accompanied with 2 g xylene assolvent. The reaction lasted 4 h. The products were analyzedwith a GC122 gas chromatograph equipped with a SE 54 capillarycolumn (30 m 0.25 mm 0.3 m) and a flame ionizationdetector A

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254

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Rx-ID: 29520138 Find similar reactions

A: 59%

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Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E.

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036 Title/Abstract Full Text View citing articles Show Details

Stage #1: B-1-hexyldiphenylborane; p-benozquinone in diethyl ether

T=20°C; Inert atmosphere; Stage #2: With water in diethyl ether

Inert atmosphere; Stage #3: ethanolamine Inert atmosphereCooling with ice; regioselective reaction; A

255

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Rx-ID: 7919878 Find similar reactions

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Bamberger

Justus Liebigs Annalen der Chemie, 1912 , vol. 390, p. 189 Full Text Show Details

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256

Synthesize Find similar Rx-ID: 541483 Find similar reactions

Asahina; Yasue

Chemische Berichte, 1936 , vol. 69, p. 643,647 Yakugaku Zasshi, 1936 , vol. 56, p. 549,554 Full Text Show Details

T=300°C; P=1 Torr;

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257

Synthesize Find similar Rx-ID: 310303 Find similar reactions

With copper oxide-chromium oxide

T=100°C; P=194910 Torr; Hydrogenation;

Williams

Journal of Organic Chemistry, 1957 , vol. 22, p. 772 Full Text View citing articles Show Details

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258

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Rx-ID: 4318454 Find similar reactions

With sodium acetate in methanol; water

T=24°C; further compounds; Equilibrium constant;

Brown,E.R. et al.

Journal of Organic Chemistry, 1971 , vol. 36, # 19 p. 2849 - 2853 Full Text View citing articles Show Details

With sodium acetate in methanol; water

T=24°C; Equilibrium constant;

Brown,E.R. et al.

Journal of Organic Chemistry, 1971 , vol. 36, # 19 p. 2849 - 2853 Full Text View citing articles Show Details

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259

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Rx-ID: 4318455 Find similar reactions

With sodium acetate in methanol; water

T=24°C; Equilibrium constant;

Brown,E.R. et al.

Journal of Organic Chemistry, 1971 , vol. 36, # 19 p. 2849 - 2853 Full Text View citing articles Show Details

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260

Synthesize Find similar Rx-ID: 5820011 Find similar reactions

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Fichter; Ris

Helvetica Chimica Acta, 1924 , vol. 7, p. 810 Full Text Show Details

bei der elektrolytischen Oxydation;

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261

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Rx-ID: 5820012 Find similar reactions

Fichter; Ris

Helvetica Chimica Acta, 1924 , vol. 7, p. 810 Full Text Show Details

bei der elektrolytischen Oxydation;

262

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Rx-ID: 4709161 Find similar reactions

83%

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With lithium chloride in pyridine

1 h; Heating;

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

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263

Synthesize Find similar Rx-ID: 8491032 Find similar reactions

A: 67% B: 9% C: 6%

Matsuo, Koji; Shiraki, Ryuji; Okubo, Masao

Journal of Physical Organic Chemistry, 1994 , vol. 7, # 10 p. 567 - 577 Title/Abstract Full Text Show Details

in tetrahydrofuran

0 deg C, 1 h, RT, 1 h, 55 deg C, 0.5 h;

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264

Synthesize Find similar Rx-ID: 4904456 Find similar reactions

A: 20% B: 43%

in toluene

Heating;

Matovic, Radomir; Cekovic, Zivorad

Gazzetta Chimica Italiana, 1997 , vol. 127, # 9 p. 483 - 488 Title/Abstract Full Text Show Details

A: 20% B: 43%

in toluene

Heating;

Matovic, Radomir; Cekovic, Zivorad

Gazzetta Chimica Italiana, 1997 , vol. 127, # 9 p. 483 - 488 Title/Abstract Full Text Show Details

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265

Synthesize Find similar Rx-ID: 2938200 Find similar reactions

A: 30% B: 20% C: 15%

With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium lauryl sulfate in acetic acid

48 h; Ambient temperature;

Chawla, H. Mohindra; Sharma, S. K.; Chakrabarty, K.; Bhanumati, S.

Tetrahedron, 1988 , vol. 44, # 4 p. 1227 - 1234 Title/Abstract Full Text View citing articles Show Details

A: 30% B: 20% C: 15%

With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium lauryl sulfate in acetic acid

48 h; Ambient temperature;

Chawla, H. Mohindra; Sharma, S. K.; Chakrabarty, K.; Bhanumati, S.

Tetrahedron, 1988 , vol. 44, # 4 p. 1227 - 1234 Title/Abstract Full Text View citing articles Show Details

A: 30% B: 20% C: 15%

With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium lauryl sulfate in acetic acid

48 h; Ambient temperature;

Chawla, H. Mohindra; Sharma, S. K.; Chakrabarty, K.; Bhanumati, S.

Tetrahedron, 1988 , vol. 44, # 4 p. 1227 - 1234 Title/Abstract Full Text View citing articles Show Details

Hide Details

A: 47 %

With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium lauryl sulfate in water; acetic acid

Chawla, H. Mohindra; Sharma, S. Kumar; Chakrabarty, K.; Bhanumati, S.

Spectr. B: 20 % Spectr. C: 15 % Spectr.

T=30°C; 2 h;

Journal of the Chemical Society, Chemical Communications, 1988 , # 2 p. 128 - 129 Title/Abstract Full Text View citing articles Show Details

A: 47 % Spectr. B: 20 % Spectr. C: 15 % Spectr.

With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium lauryl sulfate in water; acetic acid

T=30°C; 2 h;

Chawla, H. Mohindra; Sharma, S. Kumar; Chakrabarty, K.; Bhanumati, S.

Journal of the Chemical Society, Chemical Communications, 1988 , # 2 p. 128 - 129 Title/Abstract Full Text View citing articles Show Details

A: 47 % Spectr. B: 20 % Spectr. C: 15 % Spectr.

With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium lauryl sulfate in water; acetic acid

T=30°C; 2 h;

Chawla, H. Mohindra; Sharma, S. Kumar; Chakrabarty, K.; Bhanumati, S.

Journal of the Chemical Society, Chemical Communications, 1988 , # 2 p. 128 - 129 Title/Abstract Full Text View citing articles Show Details

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266

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Katsumata, Hideyuki; Okada, Toshiko; Kaneco, Satoshi; Suzuki, Tohru; Ohta, Kiyohisa

Ultrasonics Sonochemistry, 2010 , vol. 17, # 1 p. 200 - 206 Title/Abstract Full Text View citing articles Show Details

With FeCl3·6H2O; anhydrous sodium oxalate in water

T=25°C; pH=6; 0.25 h; Sonication; Kinetics; Reagent/catalystConcentrationTime;

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267

Synthesize Find similar Rx-ID: 4318456 Find similar reactions

With sodium acetate in methanol; water

T=24°C; Equilibrium constant;

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Brown,E.R. et al.

Journal of Organic Chemistry, 1971 , vol. 36, # 19 p. 2849 - 2853 Full Text View citing articles Show Details

268

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Rx-ID: 478953 Find similar reactions

With aluminium trichloride; benzene

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

269

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Rx-ID: 718229 Find similar reactions

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With zinc(II) chloride

T=200°C;

Eastman Kodak Co.

Patent: US2701197 , 1951 ; Full Text Show Details

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270

Synthesize Find similar Rx-ID: 4342826 Find similar reactions

A: 52.8% B: 6.6% C: 40.6%

With benzylamine in acetonitrile

1 h; Ambient temperature;

Mure, Minae; Klinman, Judith P.

Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8698 - 8706 Title/Abstract Full Text View citing articles Show Details

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271

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Rx-ID: 4378221 Find similar reactions

A: 15.6% B: 18.8% C: 65.6%

With oxygen in acetonitrile

1 h; Ambient temperature;

Mure, Minae; Klinman, Judith P.

Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8698 - 8706 Title/Abstract Full Text View citing articles Show Details

A: 15.6% B: 18.8% C: 65.6%

With oxygen in acetonitrile

1 h; Ambient temperature;

Mure, Minae; Klinman, Judith P.

Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8698 - 8706 Title/Abstract Full Text View citing articles Show Details

272

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Rx-ID: 295796 Find similar reactions

With palladium on activated charcoal; acetic acid

Hydrogenation;

Eastman Kodak Co.

Patent: US2728659 , 1953 ; Full Text Show Details

With hydrogen; copper (II) chromite in ethanol

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

273

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Rx-ID: 360383 Find similar reactions

With aluminium trichloride; benzene

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

274

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Rx-ID: 486463 Find similar reactions

With hydrogen bromide; acetic acid

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

With boron tribromide in dichloromethane

1) -20 deg C, 1 h; 2) rt, 3 h; Yield given;

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

275

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Rx-ID: 492900 Find similar reactions

With hydrogen bromide; acetic acid

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

276

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Rx-ID: 520360 Find similar reactions

With hydrogenchloride; amalgamated zinc

Hasan; Stedman

Journal of the Chemical Society, 1931 , p. 2112,2120 Full Text Show Details

277

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Rx-ID: 4224002 Find similar reactions

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

(i) (KO3S)2NO, acetone, (ii) NaHSO3, Et2O; Multistep reaction;

278

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Rx-ID: 4709164 Find similar reactions

65%

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With lithium chloride in pyridine

1 h; Heating;

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

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279

Synthesize Find similar Rx-ID: 8258571 Find similar reactions

Synthesize Find similar

Hasan; Stedman

Journal of the Chemical Society, 1931 , p. 2112,2120

Full Text Show Details

280

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Rx-ID: 22109926 Find similar reactions

Multi-step reaction with 2 steps 1: ZnCl2 / 130 - 140 °C 2: aqueous HCl; amalgamated zinc View Scheme

Hasan; Stedman

Journal of the Chemical Society, 1931 , p. 2112,2120 Full Text Show Details

Multi-step reaction with 3 steps 1.1: hydrogenchloride / water; tetrahydrofuran / 8 h / 20 °C 2.1: tert.-butyl lithium / tetrahydrofuran / 4.25 h / 0 - 25 °C 2.2: 12 h / 25 °C 3.1: acetic acid / water; tetrahydrofuran / 16 h View Scheme

Pulsipher, Abigail; Dutta, Debjit; Luo, Wei; Yousaf, Muhammad N.

Angewandte Chemie, International Edition, 2014 , vol. 53, # 36 p. 9487 - 9492,6 Angewandte Chemie, 2014 , vol. 126, # 36 p. 9641 - 9646,6 Title/Abstract Full Text View citing articles Show Details

281

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Rx-ID: 22375187 Find similar reactions

Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

282

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Rx-ID: 22407346 Find similar reactions

Multi-step reaction with 2 steps 1: BF3

2: H2 / copper-chromite / ethanol View Scheme

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

283

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Rx-ID: 38948725 Find similar reactions

Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 4.25 h / 0 - 25 °C 1.2: 12 h / 25 °C 2.1: acetic acid / water; tetrahydrofuran / 16 h View Scheme

Pulsipher, Abigail; Dutta, Debjit; Luo, Wei; Yousaf, Muhammad N.

Angewandte Chemie, International Edition, 2014 , vol. 53, # 36 p. 9487 - 9492,6 Angewandte Chemie, 2014 , vol. 126, # 36 p. 9641 - 9646,6 Title/Abstract Full Text View citing articles Show Details

284

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90%

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Rx-ID: 38948727 Find similar reactions

With acetic acid in tetrahydrofuran; water

16 h;

Pulsipher, Abigail; Dutta, Debjit; Luo, Wei; Yousaf, Muhammad N.

Angewandte Chemie, International Edition, 2014 , vol. 53, # 36 p. 9487 - 9492,6 Angewandte Chemie, 2014 , vol. 126, # 36 p. 9641 - 9646,6 Title/Abstract Full Text View citing articles Show Details

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285

Synthesize Find similar Rx-ID: 2703624 Find similar reactions

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A: 14% B: 284 mg C: 18%

in toluene

2.5 h; Heating;

Mori, Akira; Mametsuka, Hiroaki; Takeshita, Hitoshi

Bulletin of the Chemical Society of Japan, 1985 , vol. 58, # 7 p. 2072 - 2077 Title/Abstract Full Text Show Details

A: 14% B: 284 mg C: 18%

in toluene

2.5 h; Heating;

Mori, Akira; Mametsuka, Hiroaki; Takeshita, Hitoshi

Bulletin of the Chemical Society of Japan, 1985 , vol. 58, # 7 p. 2072 - 2077 Title/Abstract Full Text Show Details

286

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Rx-ID: 491424 Find similar reactions

With aluminium trichloride; benzene

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

287

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Rx-ID: 492956 Find similar reactions

With hydrogen bromide; acetic acid

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

288

Synthesize

Rx-ID: 498271

Find similar

Find similar reactions

With hydrogen bromide; acetic acid

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

289

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Rx-ID: 372351 Find similar reactions

With ethanol; sodium hydrogensulfite

Loev; Dawson

Journal of the American Chemical Society, 1956 , vol. 78, p. 4083,4086 Full Text View citing articles Show Details

290

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291

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Rx-ID: 390237 Find similar reactions

With sodium nitrite

anschliessendes Erhitzen mit wss. H2SO4;

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

With n-Pentyl nitrite

anschliessendes Erhitzen mit wss. H2SO4;

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

Multi-step reaction with 2 steps 1: H2SO4; Na2Cr2O7; aqueous acetone 2: ethanol; aqueous NaHSO3

View Scheme

Loev; Dawson

Journal of the American Chemical Society, 1956 , vol. 78, p. 4083,4086 Full Text View citing articles Show Details

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Rx-ID: 498048 Find similar reactions

89%

With boron tribromide in dichloromethane

T=0 - 20°C; 3 h;

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

With aluminium trichloride; benzene

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

292

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Rx-ID: 19797244 Find similar reactions

Multi-step reaction with 2 steps 1: 1.) 1.6 M n-BuLi / 1.) THF, a) 0 deg C, 30 min, b) reflux, 1.5 h, 2.) THF, reflux, 1.5 h 2: 89 percent / BBr3 / CH2Cl2 / 3 h / 0 - 20 °C View Scheme

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

293

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Multi-step reaction with 2 steps 1: 1.) 1.6 M n-BuLi / 1.) THF, a) 0 deg C, 30 min, b) reflux, 1.5 h, 2.) THF, reflux, 1.5 h 2: 89 percent / BBr3 / CH2Cl2 / 3 h / 0 - 20 °C View Scheme

Rx-ID: 19834672 Find similar reactions

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

294

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Rx-ID: 21991978 Find similar reactions

Multi-step reaction with 3 steps 1: AlCl3

2: palladium/charcoal; acetic acid / 65 °C / 2206.5 Torr / Hydrogenation 3: AlCl3; benzene View Scheme

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

295

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Rx-ID: 21996377 Find similar reactions

Multi-step reaction with 2 steps 1: und anschliessend mit wss. Na2S2O4

2: pentyl nitrite / anschliessendes Erhitzen mit wss. H2SO4

View Scheme

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

Multi-step reaction with 3 steps 1: HNO3; CHCl3

2: palladium/charcoal; ethanol / Hydrogenation 3: pentyl nitrite / anschliessendes Erhitzen mit wss. H2SO4

View Scheme

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

296

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Multi-step reaction with 2 steps

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Rx-ID: 21998089 Find similar reactions

Wasserman; Dawson

1: palladium/charcoal; ethanol / Hydrogenation 2: pentyl nitrite / anschliessendes Erhitzen mit wss. H2SO4

View Scheme

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

297

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Multi-step reaction with 2 steps 1: palladium/charcoal; acetic acid / 65 °C / 2206.5 Torr / Hydrogenation 2: AlCl3; benzene View Scheme

Rx-ID: 22016595 Find similar reactions

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details