1-Phenyl-2-propanol (P2Pol) [WYTRYIUQUDTGSX-UHFFFAOYSA-N] to 1-Phenyl-2-propanone (P2P) by Asch

Query Query 1. Query

Results

Date

15 reactions in Reaxys

2017-11-28 00h:03m:24s (EST)

Search as: As drawn, No salts, No mixtures

1/14

2017-11-28 00:06:09

Rx-ID: 1983191 View in Reaxys 1/15 Yield 99 %

Conditions & References With periodic acid, PFC in acetonitrile, Time= 2h, T= 0 °C Hunsen, Mo; Journal of Fluorine Chemistry; vol. 126; nb. 9-10; (2005); p. 1356 - 1360 View in Reaxys

99 %

With sodium hydrogencarbonate, sodium bromide in dichloromethane, T= 20 °C , Electrochemical reaction Demizu, Yosuke; Shiigi, Hirofumi; Oda, Takahisa; Matsumura, Yoshihiro; Onomura, Osamu; Tetrahedron Letters; vol. 49; nb. 1; (2008); p. 48 - 52 View in Reaxys

98 %

With chromium(VI) oxide, periodic acid in water, acetonitrile, T= 0 °C Zhao, Mangzhu; Li, Jing; Song, Zhiguo; Desmond, Richard; Tschaen, David M.; Grabowski, Edward J. J.; Reider, Paul J.; Tetrahedron Letters; vol. 39; nb. 30; (1998); p. 5323 - 5326 View in Reaxys

98 %

With periodic acid, pyridinium chlorochromate in acetonitrile, Time= 2h, T= 0 - 20 °C Hunsen, Mo; Tetrahedron Letters; vol. 46; nb. 10; (2005); p. 1651 - 1653 View in Reaxys

98 %

With dihydrogen peroxide in water, Time= 0.5h, T= 80 - 120 °C , Microwave irradiation, Green chemistry, Time, Temperature Rajabi, Fatemeh; Pineda, Antonio; Naserian, Sareh; Balu, Alina Mariana; Luque, Rafael; Romero, Antonio A.; Green Chemistry; vol. 15; nb. 5; (2013); p. 1232 - 1237 View in Reaxys

98 %

With oxone, 1-(2-(3-carboxy-4-iodophenoxy)ethyl)-3-methyl-1H-imidazol-3-ium hexafluorophosphate in water, Time= 4h, T= 70 °C Koguchi, Shinichi; Mihoya, Aya; Mimura, Minato; Tetrahedron; vol. 72; nb. 47; (2016); p. 7633 - 7637 View in Reaxys

95 %

With benzyltriphenylphosphonium peroxodisulfate in acetonitrile, Time= 0.6h, Heating, Oxidation Mohammadpoor-Baltork, Iraj; Hajipour, Abdol Reza; Mohammadi, Hasan; Bulletin of the Chemical Society of Japan; vol. 71; nb. 7; (1998); p. 1649 - 1653 View in Reaxys

95 %

With trinitratocerium(IV) bromate, Time= 0.8h, Heating Shirini, Farhad; Esm-Hosseini, Majid; Hejazi, Zoha; Synthetic Communications; vol. 35; nb. 22; (2005); p. 2913 2919 View in Reaxys

95 %

With 1-methyl-1H-imidazole, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, 4,4'-Dimethoxy-2,2'-bipyridin, ABNO, oxygen in acetonitrile, Time= 1h, T= 20 °C Steves, Janelle E.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 135; nb. 42; (2013); p. 15742 - 15745 View in Reaxys

94 %

With periodic acid, .LAMBDA.-(+)-tris(acetylacetonato)chromium(III) in acetonitrile, Time= 1h, T= 20 °C Xu, Liang; Trudell, Mark L.; Tetrahedron Letters; vol. 44; nb. 12; (2003); p. 2553 - 2555 View in Reaxys

93 %

With ammonium dichromate(VI), silica gel, zirconium(IV) chloride in hexane, Time= 1.7h, Heating

2/14

2017-11-28 00:06:09

Shirini, Farhad; Ali Zolfigol, Mohammad; Pourhabib, Akram; Journal of Chemical Research - Part S; nb. 11; (2001); p. 476 - 477 View in Reaxys 93 %

With prolinium chlorochromate in hexane, Time= 3h, Heating Mamaghani; Shirini; Parsa; Russian Journal of Organic Chemistry; vol. 38; nb. 8; (2002); p. 1113 - 1115 View in Reaxys

93 %

With iodoxybenzene, bromine, sodium nitrite in water, Time= 1h, T= 55 °C Mu, Ruizhu; Liu, Zhongquan; Yang, Zhanjun; Liu, Zhengang; Wu, Longmin; Liu, Zhong-Li; Advanced Synthesis and Catalysis; vol. 347; nb. 10; (2005); p. 1333 - 1336 View in Reaxys

93 %

With dihydrogen peroxide, poly(N-i-propylacrylamide)-phototungstic acid-based catalyst in water, Time= 6h, T= 90 °C Hamamoto, Hiromi; Suzuki, Yachiyo; Yamada, Yoichi M. A.; Tabata, Hidetsugu; Takahashi, Hideyo; Ikegami, Shiro; Angewandte Chemie - International Edition; vol. 44; nb. 29; (2005); p. 4536 - 4538 View in Reaxys

91 %

With silica gel supported bis(trimethylsilyl) chromate in dichloromethane, Time= 0.5h, T= 40 °C Lee, Jong Gun; Lee, Jung A.; Sohn, Soo Yun; Synthetic Communications; vol. 26; nb. 3; (1996); p. 543 - 549 View in Reaxys

90 %

With ammonium dichromate(VI), Mg(HSO4)2, silica gel, Time= 0.166667h, T= 20 °C Shirini; Zolfigol; Mallakpour; Hajipour; Australian Journal of Chemistry; vol. 54; nb. 6; (2001); p. 405 - 406 View in Reaxys

90 %

With potassium bromate, tetrachlorosilane, silica gel in hexane, Time= 1.16667h, Heating Shirini, Farhad; Zolfigol, Mohammad Ali; Khaleghi, Mahroo; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 178; nb. 10; (2003); p. 2107 - 2110 View in Reaxys

90 %

With tris[trinitratocerium(IV)] paraperiodate, Time= 0.33h, T= 90 °C Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. 29 - 31 View in Reaxys

90 %

With ferric nitrate, barium(II) chloride, Time= 0.416667h, T= 90 °C Habibi, Davood; Zolfigol, Mohammad Ali; Shirini, Farhad; Safaiee, Maliheh; Abedini, Masumeh; Rahmani, Payam; South African Journal of Chemistry; vol. 60; (2007); p. 17 - 19 View in Reaxys

88 %

With periodic acid, pyridinium chlorochromate in acetonitrile, Time= 1h, T= 0 °C Romanov-Michailidis, Fedor; Sedillo, Kassandra F.; Neely, Jamie M.; Rovis, Tomislav; Journal of the American Chemical Society; vol. 137; nb. 28; (2015); p. 8892 - 8895 View in Reaxys

86 %

With ammonium dichromate(VI), aluminum(III) hydrogen sulfate, silica gel, Time= 1.2h, T= 20 °C Shirini, Farhad; Zolfigol, Mohammad A.; Abedini, Masoumeh; Salehi, Peyman; Mendeleev Communications; vol. 13; nb. 6; (2003); p. 265 - 267 View in Reaxys

85 %

With pyridine, trichloroisocyanuric acid in acetone, Time= 0.333333h Hiegel; Nalbandy; Synthetic Communications; vol. 22; nb. 11; (1992); p. 1589 - 1595 View in Reaxys

85 %

Stage 1: With (-N(SO2C8F17)-(biphenyl-2,2'-diyl)-O-)AlCH3 in toluene, Time= 0.5h, T= 21 °C Stage 2: With pivalaldehyde in toluene, Time= 3h, T= 21 °C , Oppenauer oxidation, Further stages.

3/14

2017-11-28 00:06:09

Ooi, Takashi; Otsuka, Hidehito; Miura, Tomoya; Ichikawa, Hayato; Maruoka, Keiji; Organic Letters; vol. 4; nb. 16; (2002); p. 2669 - 2672 View in Reaxys 85 %

With C29H35Cl2IrN2O2, sodium acetate in 2,2,2-trifluoroethanol, Time= 20h, Inert atmosphere, Reflux, Schlenk technique Gülcemal, Süleyman; Gülcemal, Derya; Whitehead, George F. S.; Xiao, Jianliang; Chemistry - A European Journal; vol. 22; nb. 30; (2016); p. 10513 - 10522 View in Reaxys

84 %

32.A : A. l-phenylpropan-2-one A. l-phenylpropan-2-one [00367] A solution of l-phenylpropan-2-ol (2.72 g, 20 mmol) in CH2CI2 (20 mL) was added pyridinium chlorochromate (PCC, 5.4 g, 25 mmol) at 0 °C and the mixture was stirred for 3 h. The mixture was concentrated and purified by flash column chromatography (PE/EtOAc = 20: 1) to give the title compound (2.3 g, 84percent) as a yellow oil. With pyridinium chlorochromate in dichloromethane, Time= 3h, T= 0 °C Patent; QUANTICEL PHARMACEUTICALS, INC; NIE, Zhe; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan; WO2014/89364; (2014); (A1) English View in Reaxys

83 %

With pyridine, tri-n-butyl phosphine oxide, oxygen, palladium diacetate in toluene, Time= 24h, T= 80 °C , p= 750.075Torr , Molecular sieve Gowrisankar, Saravanan; Neumann, Helfried; Goerdes, Dirk; Thurow, Kerstin; Jiao, Haijun; Beller, Matthias; Chemistry - A European Journal; vol. 19; nb. 47; (2013); p. 15979 - 15984 View in Reaxys

80 %

With sodium carbonate, acetone, BQC, bis(1,5-cyclooctadiene)diiridium(I) dichloride in water, Time= 17h, T= 90 °C Ajjou, Abdelaziz Nait; Pinet, Jean-Louis; Canadian Journal of Chemistry; vol. 83; nb. 6-7; (2005); p. 702 - 710 View in Reaxys

78 %

Typical procedure for the oxidation of alcohols General procedure: A solution of BTC (0.41 g, 1.39 mmol) in dry CH2Cl2 (5 mL) was cooled in an ice-salt bath under an atmosphere of N2. A solution of I (1.24 g, 4.17 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at −15 °C. Stirring was continued for 0.5 h, and a solution of benzyl alcohol (0.3 g, 2.78 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at−15 °C. After stirring for 0.5 h, Et3N (0.84 g, 8.34 mmol) was added slowly while the temperature should be controlled below −15 °C. When the reaction was completed, 10percent HCl solution in water was added dropwise until the pH of the reaction solution reached 2 under ice bath. The mixture was extracted with nhexane or petroleum ether (10 mL x 2),decanted. The product was acquired after organic layer was concentrated and purified by flash chromatography (SiO2; n-hexane). (0.27 g, 92percent). The water layer was used for the recovery of V and the excess I. Stage 1: With bis(trichloromethyl) carbonate, 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine in dichloromethane, Time= 1h, T= -15 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, T= -15 °C , Inert atmosphere, Swern Oxidation Ye, Xiaojing; Fu, Hongliang; Ma, Jiahao; Zhong, Weihui; Synthetic Communications; vol. 46; nb. 10; (2016); p. 885 - 892 View in Reaxys

77 %

Stage 1: With oxalyl dichloride, dimethyl sulfoxide in dichloromethane, T= -78 °C , Inert atmosphere, Swern oxidation Stage 2: With triethylamine in dichloromethane, T= 20 °C , Cooling, Inert atmosphere, Swern oxidation Ema, Tadashi; Ura, Norichika; Yoshii, Masataka; Korenaga, Toshinobu; Sakai, Takashi; Tetrahedron; vol. 65; nb. 46; (2009); p. 9583 - 9591 View in Reaxys

76 %

20.1 : Step 1 phcnylpropan-2-one Step 1 Dess-Martin reagent (9.3 g, 22.0 mniol) was added into a solution of I -phenylpropan-2-ol (2.0 g, 15 mmol) in DCM (20 mL) at room temperature. The mixture was stirred at room temperature for 12 his and washed with

4/14

2017-11-28 00:06:09

Na2S2O3 ag. solution (20 mL), NaHCO3 aq. solution (20 mE). The organic phase was dried over anhydrous Na2SO4 and then filtered. The filtrate was concentrated and theresidue was purified by flash column chromatography on silica gel eluting with 20percent EtOAc in hexanes to give the desired product (1.5 g, 76percent yield) as colorless oil. ‘H NMR (400 MHz, CDC13) 6 7.35 -7.32 (m, 211), 7.29— 7.27 (m, 111), 7.25 - 7.19 (m, 2H), 3.69 (s, 2H), 2.15 (s, 311). With Dess-Martin periodane in dichloromethane, Time= 12h, T= 20 °C Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; LAI, Kwong Wah; LIANG, Jun; ZHANG, Birong; LABADIE, Sharada; ORTWINE, Daniel; DRAGOVICH, Peter; KIEFER, James; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; (263 pag.); WO2016/57924; (2016); (A1) English View in Reaxys 75 %

With potassium bromide in water, acetonitrile, Time= 12h, T= 20 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Zhdankin, Viktor V.; Synlett; nb. 18; (2010); p. 2771 - 2774 View in Reaxys

72 %

With caesium carbonate in para-xylene, Time= 24h, Reflux, Reagent/catalyst Shapiro, Leora; Avnir, David; ChemCatChem; vol. 9; nb. 5; (2017); p. 816 - 823 View in Reaxys

70 %

With potassium bromate, zirconium(IV) oxychloride in acetonitrile, Time= 0.5h, Heating Shirini, Farhad; Zolfigol, Mohammad Ali; Mollarazi, Esmail; Synthetic Communications; vol. 35; nb. 11; (2005); p. 1541 - 1545 View in Reaxys

70 %

With Dess-Martin periodane in dichloromethane, Time= 2h, T= 0 - 20 °C , Inert atmosphere Denton, Justin R.; Davies, Huw M. L.; Organic Letters; vol. 11; nb. 4; (2009); p. 787 - 790 View in Reaxys

50 %

With tert.-butylhydroperoxide, tris(triphenylphosphine)ruthenium(II) chloride in benzene, Time= 20h, Ambient temperature Murahashi; Naota; Synthesis; nb. 4; (1993); p. 433 - 440 View in Reaxys

50 %

With tert.-butylhydroperoxide, tris(triphenylphosphine)ruthenium(II) chloride, Time= 20h Murahashi; Naota; Russian Journal of Organic Chemistry; vol. 32; nb. 2; (1996); p. 203 - 213 View in Reaxys

40 %

With [Pd(N,N'-bis(2,6-(diisopropyl)phenyl)imidazol-2-ylidene)(PCy3)], oxygen, acetic acid in toluene, Time= 14.5h, T= 60 °C , p= 760.051Torr , Molecular sieve Jurcik, Vaclav; Schmid, Thibault E.; Dumont, Quentin; Slawin, Alexandra M. Z.; Cazin, Catherine S. J.; Dalton Transactions; vol. 41; nb. 40; (2012); p. 12619 - 12623,5 View in Reaxys

14 %

With tert.-butylhydroperoxide, Rh+(diphos) in methanol, Time= 24h, T= 70 °C , several conditions investigated and other solvent also investigated, Product distribution Mueller, Paul; Idmoumaz, Hamid; Journal of Organometallic Chemistry; vol. 345; (1988); p. 187 - 200 View in Reaxys With oxalyl dichloride, dimethyl sulfoxide, triethylamine, 1.) dichloromethane, -70 deg C, 15 min; 2.) r.t., 15 min, Multistep reaction Takano, Seiichi; Inomata, Kohei; Samizu, Kiyohiro; Tomita, Shun'ichi; Yanase, Masashi; et al.; Chemistry Letters; (1989); p. 1283 - 1284 View in Reaxys

85 % Spectr.

With 3,3-dimethyldioxirane in acetone, T= 25 °C , Rate constant

5/14

2017-11-28 00:06:09

Baumstark, Alfons L.; Kovac, Franci; Vasquez, Pedro C.; Canadian Journal of Chemistry; vol. 77; nb. 3; (1999); p. 308 - 312 View in Reaxys 66 % Chromat.

With mukaiyama’s reagent, zinc(II) oxide in dichloromethane, Time= 0.5h, T= 20 °C Matsuo, Jun-Ichi; Kitagawa, Hideo; Iida, Daisuke; Mukaiyama, Teruaki; Chemistry Letters; nb. 2; (2001); p. 150 151 View in Reaxys With 3,3-dimethyldioxirane in acetone, T= 0 °C , Kinetics Angelis, Yiannis S.; Hatzakis, Nikos S.; Smonou, Ioulia; Orfanopoulos, Michael; Tetrahedron Letters; vol. 42; nb. 22; (2001); p. 3753 - 3756 View in Reaxys

66 % Chromat.

With mukaiyama’s reagent, zinc(II) oxide in dichloromethane, Time= 0.5h, T= 20 °C Matsuo, Jun-Ichi; Iida, Daisuke; Tatani, Kazuya; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol. 75; nb. 2; (2002); p. 223 - 234 View in Reaxys With tert.-butylhydroperoxide, tetrabutyl-ammonium chloride, BQC, sodium carbonate in water, Time= 24h, T= 20 °C Ferguson, Gabriel; Ajjou, Abdelaziz Nait; Tetrahedron Letters; vol. 44; nb. 51; (2003); p. 9139 - 9142 View in Reaxys Reaction Steps: 2 1: 91 percent / CAN; 1-n-butylpyridinium chloroferrate / 0.5 h / 20 °C 2: 92 percent / 1-n-butylpyridinium chloroferrate; pyridinium chlorochromate / 0.58 h / 50 °C With ammonium cerium(IV) nitrate, 1-n-butylpyridinium tetrachloroferrate, pyridinium chlorochromate Khosropour, Ahmad R.; Khodaei, Mohammad M.; Ghaderi, Sattar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 3; (2006); p. 326 - 330 View in Reaxys Reaction Steps: 2 1: 91 percent / CAN; 1-n-butylpyridinium chloroferrate / 0.5 h / 20 °C 2: 87 percent / 1-n-butylpyridinium chloroferrate; pyridinium chlorochromate / 0.47 h / 50 °C With ammonium cerium(IV) nitrate, 1-n-butylpyridinium tetrachloroferrate, pyridinium chlorochromate Khosropour, Ahmad R.; Khodaei, Mohammad M.; Ghaderi, Sattar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 3; (2006); p. 326 - 330 View in Reaxys

6 %Chromat.

With μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III), iodosylbenzene in dichloromethane, Time= 3.5h, T= 20 °C Geraskin, Ivan M.; Luedtke, Matthew W.; Neu, Heather M.; Nemykin, Victor N.; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 49; nb. 52; (2008); p. 7410 - 7412 View in Reaxys 5.A :1-Phenyl-2-propanol (10 mL, 71 mmol) was dissolved in acetone (800 mL), cooled to 10° C. and Jones reagent was added slowly until an orange color persisted. After 5 min, 2-propanol was added to destroy the excess chromium reagent. The reaction mixture was diluted with Et2O (500 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted once more with Et2O (200 mL). The ether extracts were combined and washed with brine (2*100 mL), dried over MgSO4 and evaporated under reduced pressure. The product was obtained as a yellow oil that was used directly in the next step. Stage 1: With Jone's reagent in acetone, Time= 0.0833333h, T= 10 °C Stage 2: With isopropyl alcohol in acetone Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); (A1) English

6/14

2017-11-28 00:06:09

View in Reaxys Typical procedure of oxidation of alcohols with PS-DCIB 2 in CH3CN-H2O: To a solution of benzyl alcohol 13a (0.021 g, 0.2 mmol) and pyridine (0.052 mL, 0.6mmol) in CH3CN-H2O (2 mL, v/v =1:1) was added PS-DICB 2 (0.223 g, 0.3 mmol) and TEMPO (0.003 g, 0.02 mmol) at room temperature, and the mixture was warmed up to 50 °C and magnetically stirred until the alcohol was consumed (monitored by TLC). The mixture was filtered, and the PS-IB resin was washed with CH3CN (3 x 1 mL) and collected for reuse. To the filtrate was added 2 mL of a standard solution of 2,4-dinitrophenylhydrazine (prepared from 3 g 2,4-DNP, 15 mL concd H2SO4, 70 mL EtOH,and 20 mL H2O). The precipitate was filtered, washed with water and 95percent ethanol, dried in vacuum to give 2,4-dinitrophenyl-hydrazone 14a (0.053 g, 92percent) With pyridine, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in water, acetonitrile, Time= 3.5h, T= 50 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Middleton, Kyle; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 52; nb. 16; (2011); p. 1952 - 1955 View in Reaxys 1 :Preparation of l-phenylpropan-2-one (3B): A stock solution of periodic acid/chromium trioxide was prepared according to WO 99/52850 by dissolving periodic acid (11.4 g, 50.0 mmol) and chromium trioxide (23 mg, 1.2 mol percent) in wet acetonitrile (0.75percent H20) to a volume of 114 mL. This stock solution (104.5 mL) was added to a solution of l-phenylpropan-2-ol (3A) (5.0 g, 36.71 mmol) in wet acetonitrile (150 mL, 0.75percent H20) at 0 °C over 1 h, maintaining internal temperature below 5 °C. The reaction was quenched with K2HP04 (11.5 g, 50.5 mmol) in H20 (60 mL).Dichloromethane was added and organic layer separated and washed with brine/H20 (2 x 100 mL), followed by saturated NaHS03/brine. The organic layer was dried(MgS04), filtered and concentrated to give 3B as a yellow oil (5.1 g). 'H-NMR: 300 MHz, (CDC13) δ 7.35-7.10 (m, 5H), 3.65 (s, 2H), 2.11 (s, 3 H). With chromium(VI) oxide, periodic acid in water, acetonitrile, Time= 1h, T= 0 - 5 °C Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BJORNSON, Kyla; GUO, Hongyan; HALCOMB, Randall, L.; LINK, John, O.; MCFADDEN, Ryan; MITCHELL, Michael, L.; ROETHLE, Paul; TRENKLE, James, D.; VIVIAN, Randall, W.; XU, Lianhong; WO2012/3497; (2012); (A1) English View in Reaxys 82 %Spectr.

With oxygen in 1,4-dioxane, Time= 22h, T= 80 °C Asao, Naoki; Hatakeyama, Naoya; Menggenbateer; Minato, Taketoshi; Ito, Eisuke; Hara, Masahiko; Kim, Yousoo; Yamamoto, Yoshinori; Chen, Mingwei; Zhang, Wei; Inoue, Akihisa; Chemical Communications; vol. 48; nb. 38; (2012); p. 4540 - 4542 View in Reaxys

94 %Spectr.

With C10H16NO5, potassium carbonate, bis-[(trifluoroacetoxy)iodo]benzene, Time= 0.75h, T= 20 °C , Catalytic behavior, Reagent/catalyst Hamada, Shohei; Furuta, Takumi; Wada, Yoshiyuki; Kawabata, Takeo; Angewandte Chemie - International Edition; vol. 52; nb. 31; (2013); p. 8093 - 8097; Angew. Chem.; vol. 125; nb. 31; (2013); p. 8251 - 8255,5 View in Reaxys

102 mg

4.1 : Production Example 4 Synthesis of Compound 9 (1) 1-Phenyl-2 -propanol (h) (428 mg) was dissolved in dichloromethane (16 mL) , subsequently molecular sieves 4A (400 mg) , N-methylmorpholine (1.10 g) andtetrapropylammonium perruthenate (110 mg) were added thereto and the solution was stirred for 24 hours at room temperature under nitrogen atmosphere. The reaction solution was filtered using a silica gel short column, and the filtrate was dried under reduced pressure and subsequently purified by silica gel chromatography, thereby obtaining ketone (i) (102 mg) . With 4-methyl-morpholine, tetrapropylammonium perruthennate in dichloromethane, Time= 24h, T= 20 °C , Molecular sieve, Inert atmosphere Patent; KAO CORPORATION; KINOSHITA, Kazuki; SHIRAI, Tomohiro; KUMIHASHI, Kentaro; FUJIHARA, Hirohisa; MUGITA, Nanae; WO2013/103155; (2013); (A1) English View in Reaxys With dimethyl sulfoxide, N-ethyl-N,N-diisopropylamine, trifluoroacetic anhydride in dichloromethane, T= -20 °C , Flow reactor

7/14

2017-11-28 00:06:09

Van Der Linden, Jacobus J. M.; Hilberink, Peter W.; Kronenburg, Claudia M. P.; Kemperman, Gerardus J.; Organic Process Research and Development; vol. 12; nb. 5; (2008); p. 911 - 920 View in Reaxys Reaction Steps: 2 1: Candida antarctica lipase B / toluene / 20 °C / |Enzymatic reaction 2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / |Enzymatic reaction With Candida antarctica lipase B, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 3 1: Candida antarctica lipase B / toluene / 20 °C / |Enzymatic reaction 2: potassium hydoxide; water / methanol 3: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / |Enzymatic reaction With Candida antarctica lipase B, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, water, nicotinamide adenine dinucleotide phosphate, potassium hydoxide in methanol, toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 32 %Chromat.

With phosphomolybdic acid, oxygen, tetrabutylammonium acetate, palladium diacetate in ethyl acetate, Time= 1h, T= 100 °C , p= 22502.3Torr Dornan, Laura M.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 5; nb. 3; (2015); p. 1428 - 1432 View in Reaxys

100 %Spectr.

General procedure: Typical procedure for oxidationof alcohols using PIB-bound IBX. Thedesired alcohol (0.5 mmol) and 2 equivalents of of PIB-bound IBX were dissolved inheptane. Then 2 equivalents of boron trifluoride diethyl etherate was thenadded into the reaction mixture and the reaction mixture was stirred at roomtemperature for 30 min. Analiquot of the heptane reaction mixture was taken and diluted with CDCl3to determine the conversion of the substrate to product by 1H NMR spectroscopy. Kinetic studies where areaction mixture in CDCl3 was directly analyzed by 1H NMRspectroscopy had previously been used to show that this was a sufficient timefor complete conversion of alcohols to their product aldehyde or ketone Asdescribed above, the products were separated from the heptane solution of anyunreacted or spent oxidant by an extraction with acetonitrile. The heptane from the solution ofpolyisobutylene-bound substrates was then removed at reduced pressure and the PIBspecies isolated were reoxidized as described above. The reoxidized PIB-boundIBX was always characterized by 1H NMR and the ratio of PIB-boundIBX to the ester of PIB-bound 2-iodobenzoic acid was always calculated before asubsequent cycle. With boron trifluoride diethyl etherate, C79H149IO4 in n-heptane, Time= 0.5h, T= 25 °C Samunual, Peerada; Bergbreiter, David E.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3272 - 3276 View in Reaxys

HO H

Rx-ID: 11275715 View in Reaxys 2/15 Yield 23.1 % Chromat.

Conditions & References With 1,4-dihydronicotinamide adenine dinucleotide, NAD, RE-ADH/LK-ADH in phosphate buffer, Time= 24h, T= 30 °C Gruber, Christian C.; Nestl, Bettina M.; Gross, Johannes; Hildebrandt, Petra; Bornscheuer, Uwe T.; Faber, Kurt; Kroutil, Wolfgang; Chemistry - A European Journal; vol. 13; nb. 29; (2007); p. 8271 - 8276 View in Reaxys

8/14

2017-11-28 00:06:09

With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in aq. buffer, T= 50 °C , pH= 8.9, Enzymatic reaction, Kinetics, Reagent/catalyst, enantiospecific reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris–HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee. With NADPH, nicotinamide adenine dinucleotide phosphate, W110G TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159 View in Reaxys With alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A variant, NADPH oxidase from Bacillus subtilis, nicotinamide adenine dinucleotide phosphate, catalase in aq. buffer, Time= 24h, T= 30 °C , pH= 7.5, Enzymatic reaction, Catalytic behavior, pH-value Knaus, Tanja; Cariati, Luca; Masman, Marcelo F; Mutti, Francesco G.; Organic and Biomolecular Chemistry; vol. 15; nb. 39; (2017); p. 8313 - 8325 View in Reaxys

HO H

Rx-ID: 5195147 View in Reaxys 3/15 Yield 66 %

Conditions & References With (1R)-N-oxyl-1-(N-benzylcarbamoyl)-8-azabicyclo[3.2.1]octane, sodium hydrogencarbonate, sodium bromide in dichloromethane, water, T= 0 °C , Electrochemical reaction, optical yield given as percent ee, enantioselective reaction Demizu, Yosuke; Shiigi, Hirofumi; Mori, Hiroyuki; Matsumoto, Kazuya; Onomura, Osamu; Tetrahedron Asymmetry; vol. 19; nb. 23; (2008); p. 2659 - 2665 View in Reaxys

40 %

With Sphingomonas paucimobilis NCIMB 8195 in water, N,N-dimethyl-formamide, Time= 120h Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys

44 % Chromat.

With Geotrichum candidum IFO 4597 cells on BL-100 polymer, cyclohexanone in hexane, Time= 24h, T= 30 °C , Oxidation Nakamura, Kaoru; Inoue, Yuko; Matsuda, Tomoko; Misawa, Ibuki; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2397 - 2402 View in Reaxys

50.9 % Chromat.

With air, (R,R)-(nitroso)(salen)ruthenium(II) chloride in toluene, Time= 17h, T= 20 °C , Irradiation, resolution of racemate; oxidation Masutani, Kouta; Uchida, Tatsuya; Irie, Ryo; Katsuki, Tsutomu; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5119 - 5123

9/14

2017-11-28 00:06:09

View in Reaxys With [bis(acetoxy)iodo]benzene, tetraethylammonium bromide, [Mn{CHPhNCH[OC6H2(t-Bu)2]}2]PF6 in water, Time= 0.5h, T= 20 °C , Product distribution, Further Variations: Catalysts, reaction times Sun, Wei; Wang, Hongwang; Xia, Chungu; Li, Jingwei; Zhao, Peiqing; Angewandte Chemie - International Edition; vol. 42; nb. 9; (2003); p. 1042 - 1044 View in Reaxys With lyophilized cells of Rhodococcus ruber DSM 44541, acetone in phosphate buffer, Time= 24h, T= 24 °C , pH= 8.0, Title compound not separated from byproducts Stampfer, Wolfgang; Kosjek, Birgit; Faber, Kurt; Kroutil, Wolfgang; Journal of Organic Chemistry; vol. 68; nb. 2; (2003); p. 402 - 406 View in Reaxys With air, chiral Ru(salen)(nitrosyl) complex in chloroform, Time= 11h, T= 20 °C , UV-irradiation, Kinetics Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys With air, chiral Ru(salen)(nitrosyl) complex in chloroform, T= 20 °C , UV-irradiation, Title compound not separated from byproducts. Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant, NADP in acetone, Time= 24h, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p. 1459 - 1463 View in Reaxys

HO H

Rx-ID: 38389798 View in Reaxys 4/15 Yield

Conditions & References With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in aq. buffer, T= 50 °C , pH= 8.9, Enzymatic reaction, Kinetics, Reagent/catalyst, enantiospecific reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris–HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee. With NADPH, NADP+, W110G TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159

10/14

2017-11-28 00:06:09

View in Reaxys

Rx-ID: 38471071 View in Reaxys 5/15 Yield 80 %

Conditions & References With tetra-n-butylammonium acetate, palladium diacetate, HSA in toluene, Time= 6h, T= 100 °C , p= 22502.3Torr Dornan, Laura M.; Clendenning, Grainne M. A.; Pitak, Mateusz B.; Coles, Simon J.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2526 - 2534 View in Reaxys

HO H

Rx-ID: 11097767 View in Reaxys 6/15 Yield

Conditions & References With [bis(acetoxy)iodo]benzene, potassium bromide in dichloromethane, water, Time= 1h, T= 20 °C Sun, Wei; Wu, Xiaomei; Xia, Chungu; Helvetica Chimica Acta; vol. 90; nb. 3; (2007); p. 623 - 626 View in Reaxys Stage 1: With C28H36ClMnN2O2, potassium acetate in dichloromethane, water, Time= 0.0833333h Stage 2: With N-bromosuccinmide in dichloromethane, water, Time= 2h, T= 20 °C , Kinetics, enantioselective reaction Xu, Daqian; Wang, Shoufeng; Shen, Zhiqiang; Xia, Chungu; Sun, Wei; Organic and Biomolecular Chemistry; vol. 10; nb. 14; (2012); p. 2730 - 2732 View in Reaxys Typical procedure for the OKR of racemic secondary alcohols with C2-PhI(OAc)2 system General procedure: Typical procedure for the OKR of racemic secondary alcohols with C2-PhI(OAc)2 system To a 5 mL glass reactor substrate (0.25 mmol), catalyst C2 (0.005 mmol, 2 molpercent), CH2Cl2 (0.3 mL) and H2O (0.6 mL) were added and the resulting mass was magnetically stirred for 5 min. To the above stirring mass, KBr (4 molpercent) was added at room temperature. The reaction mixture was then cooled to 15 °C and PhI(OAc)2 (0.7 equiv.) was added slowly in small fractions over 15 min and stirring was continued to the specified time. After the completion of the reaction, catalyst was precipitated out by the addition of hexane to the reaction mixture. The recovered catalyst was dried and stored for future use. An aliquot of organic layer was subjected to HPLC analysis to determine enantiomeric excess (ee) of the product. The resulting ketone and enantio-enriched secondary alcohol were separated by silica gel flash chromatography. With [bis(acetoxy)iodo]benzene, C36H50ClMnN2O6, potassium bromide in dichloromethane, water, Time= 0.5h, T= 15 °C , Reagent/catalyst Bera, Prasanta Kumar; Maity, Nabin Ch.; Abdi, Sayed H.R.; Khan, Noor-Ul H.; Kureshy, Rukhsana I.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 467; (2013); p. 542 - 551 View in Reaxys

HO H

Rx-ID: 34106261 View in Reaxys 7/15 Yield 52 %

Conditions & References With Arthrobacter atrocyaneus in N,N-dimethyl-formamide, Time= 72h, T= 32 °C , Microbiological reaction, enantioselective reaction

11/14

2017-11-28 00:06:09

Silva, Camila R.; Souza, Juliana C.; Araujo, Lidiane S.; Kagohara, Edna; Garcia, Thais P.; Pelizzari, Vivian H.; Andrade, Leandro H.; Journal of Molecular Catalysis B: Enzymatic; vol. 83; (2012); p. 23 - 28 View in Reaxys

CrO 3

Rx-ID: 28819264 View in Reaxys 8/15 Yield

Conditions & References

61 %

Stage 1: in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: in dichloromethane, T= 20 °C , Inert atmosphere Balamurugan, Rengarajan; Gudla, Vanajakshi; Organic Letters; vol. 11; nb. 14; (2009); p. 3116 - 3119 View in Reaxys

Rx-ID: 9778030 View in Reaxys 9/15 Yield

Conditions & References

60 % Chromat.

With sodium hypochlorite, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, T= 20 °C , pH= 8.5 - 9 Bright, Zack R.; Luyeye, Cedric R.; Morton, Angela Ste. Marie; Sedenko, Marina; Landolt, Robert G.; Bronzi, Matthew J.; Bohovic, Katherine M.; Gonser, M. W. Alex; Lapainis, Theodore E.; Hendrickson, William H.; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 684 - 687 View in Reaxys

2H 2H

Rx-ID: 8815234 View in Reaxys 10/15 Yield

Conditions & References With 3,3-dimethyldioxirane in acetone, T= 0 °C , Kinetics Angelis, Yiannis S.; Hatzakis, Nikos S.; Smonou, Ioulia; Orfanopoulos, Michael; Tetrahedron Letters; vol. 42; nb. 22; (2001); p. 3753 - 3756 View in Reaxys

H NH O

Rx-ID: 3737785 View in Reaxys 11/15 Yield 3 %, 2 %, 22 %, 16 %, 14 %

Conditions & References With Titanium(IV) oxide, silver sulphate, Time= 5h, Ambient temperature, Irradiation, TiO2-photosensitized oxidation Baciocchi, Enrico; Rol, Cesare; Sebastiani, Giovanni V.; Taglieri, Luca; Journal of Organic Chemistry; vol. 59; nb. 18; (1994); p. 5272 - 5276 View in Reaxys

12/14

2017-11-28 00:06:09

H O

Rx-ID: 1983187 View in Reaxys 12/15 Yield

Conditions & References With ammonium peroxydisulfate, copper diacetate, sodium acetate in acetonitrile, T= 100 °C , Yield given. Yields of byproduct given Walling, Cheves; El-Taliawi, Gamil M.; Zhao, Chengxue; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4914 - 4917 View in Reaxys With ammonium peroxydisulfate, copper diacetate, sodium acetate in acetonitrile, T= 100 °C , Yield given Walling, Cheves; El-Taliawi, Gamil M.; Zhao, Chengxue; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4914 - 4917 View in Reaxys O O

Rx-ID: 2340690 View in Reaxys 13/15 Yield

Conditions & References With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 7h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys With potassium hydroxide, Ru(O2CCF3)2(CO)(PPh3)2, Time= 24h, T= 140 °C , ΔG (gas), Equilibrium constant, Thermodynamic data Strohmeier, Walter; Graser, Barbara; Zeitschrift fuer Physikalische Chemie (Muenchen, Germany); vol. 121; (1980); p. 121 - 130 View in Reaxys With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 24h, T= 140 °C , variat. KOH concentration, Equilibrium constant, Rate constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys

Rx-ID: 3382701 View in Reaxys 14/15 Yield

Conditions & References With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 35h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 22h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys

13/14

2017-11-28 00:06:09

OH HO

S OO

HO H

Na2Cr2O7

Rx-ID: 8261826 View in Reaxys 15/15 Yield

Conditions & References Levene; Walti; Journal of Biological Chemistry; vol. 90; (1931); p. 81,86 View in Reaxys

14/14

2017-11-28 00:06:09