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20 reactions in Reaxys
2017-10-15 00h:07m:23s (EST)
OH
Search as: As drawn, No salts, No mixtures, No isotopes, No charges, No radicals
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HO
OH
Rx-ID: 38785279 View in Reaxys 1/20 Yield
Conditions & References General procedure: General procedure for the hydroxylation of arenes: A borosilicate flask was equipped with a magnetic stir bar and neat or solid arene (0.2-0.8 mmol) was added. Addition of HFIP or TFE (2-5 mL) to provide a 0.2 M solution was followed by the addition of solid phthaloyl peroxide (1, 1.3 equiv.) in portions over 90 seconds. The reaction flask was placed in a heated oil bath (23-50 °C). After 3-24 hours, the reaction was removed from the oil bath and cooled to ambient temperature (23 °C). The reaction was then concentrated and under positive N2 pressure (to avoid potential air oxidation of the phenolic product) MeOH (3 mL) and saturated aqueous NaHC03 solution (0.2 mL) were added and the solution was stirred. After 12 hours, the reaction was quenched with pH 7.0 phosphate buffer (5 mL) and extracted with EtOAc (10 mL x 3) and the combined organic layers were washed with brine (5 mL), dried over Na2S04, and concentrated. The crude material was purified by silica gel column chromatography to afford the desired phenolic product. Stage 1: With 2,3-benzodioxin-1,4-dione, Heating Stage 2: With sodium hydrogencarbonate in methanol, water, Time= 12h, Inert atmosphere, Overall yield = 53 percent Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; AXELROD, Abram; JOHNSON, Trevor, C.; SIEGEL, Dionicio; CAMELIO, Andrew, M.; YUAN, Changxia; ELIASEN, Anders; WO2014/158209; (2014); (A1) English View in Reaxys
HO
OH
Rx-ID: 36063259 View in Reaxys 2/20 Yield
Conditions & References General procedure for the hydroxylation of arenes. General procedure: A borosilicate flask was equipped with a magnetic stir bar, and neat or solid arene (0.2– 0.8mmol) was added. Addition of hexafluoroisopropanol or trifluoroethanol (2–5 ml) to providea 0.2M solution was followed by the addition of solid phthaloyl peroxide (1, 1.3 equiv.) in portions over 90 s. The reaction flask was placed in a heated oil bath (23–50 °C). After 3–24 h, the flask was removed from the oil bath and cooled to ambient temperature (23 °C). The reaction was then concentrated, and under positive N2 pressure (to avoid potential air oxidation of the phenolic product) MeOH (3 ml) and saturated aqueous NaHCO3 solution (0.2 ml) were added and the solution was stirred. After 12 h, the reaction was quenched with phosphate buffer (5 ml, pH 7.0) and extracted with EtOAc (10 ml x 33), and the combined organic layers were washed with brine (5 ml), dried over Na2SO4 and concentrated. The crude material was purified by silica-gel column chromatography to afford the desired phenolic product. For full experimental details and characterization of new compounds, see Supplementary Information. Stage 1: With 2,3-benzodioxin-1,4-dione, Heating Stage 2: With water, sodium hydrogencarbonate in methanol, T= 40 °C , Overall yield = 53 percent Yuan, Changxia; Liang, Yong; Hernandez, Taylor; Berriochoa, Adrian; Houk, Kendall N.; Siegel, Dionicio; Nature; vol. 499; nb. 7457; (2013); p. 192 - 196 View in Reaxys
OH
O
OH
Rx-ID: 11169853 View in Reaxys 3/20 Yield 66 %
Conditions & References I.I-III.I-Q :Example I-IIIPreparation of Compound 305, and 306General Procedure I-QNaCNBH3 (6.4 g, 101.1 mmol) was added to the mixture of compound I-IIIa (5.0 g, 33.7 mmol) and zinc iodide (32.3 g, 101.1 mmol) in dichloro-
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ethane (100 mL), the mixture was stirred at reflux for 2 hours. The reaction mixture was then filtered through SiO2 while still warm, eluding further with dichloroethane. The filtrate was collected and concentrated under reduced pressure. The residue was added to diethyl ether and the resulting white precipitate was filtered off. The filtrate was collected and concentrated in vacuo, then purified by flash column to give compound I-IIIb (3 g, yield: 66percent). 1H NMR (400 MHz, CDCl3): 7.02 (m, 1H), 6.80 (d, J=5.2 Hz, 1H), 6.61 (m, 1H), 2.91 (m, 4H), 2.05 (m, 2H). With sodium cyanoborohydride, zinc(II) iodide in anhydrous dichloroethane, Time= 2h, Reflux Patent; InterMune, Inc.; US2011/152246; (2011); (A1) English View in Reaxys 42 %
With sodium cyanoborohydride, zinc(II) iodide in 1,2-dichloro-ethane, Time= 2h, Heating Pettersson, Ingrid; Ebdrup, Soren; Havranek, Miroslav; Pihera, Pavel; Korinek, Marek; Mogensen, John P.; Jeppesen, Claus B.; Johansson, Eva; Sauerberg, Per; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 16; (2007); p. 4625 - 4629 View in Reaxys 7 : Preparation of Indan-4-ol (compound 7A) Preparation of Indan-4-ol (compound 7A) A mixture of 4-hydroxy-indan-1-one (5.0 g, 33.7 mmol), sodium cyanoborohydride (6.4 g, 101.1 mmol), and zinc iodide (32.3 g, 101.1 mmol) in dichloroethane, was heated at reflux for two hours. The reaction mixture was then filtered through 50 g SiO2 while still warm, eluding further with dichloroethane. The filtrate was collected and concentrated under vacuum. The residue was added to diethyl ether and the resulting white precipitate was filtered off. The filtrate was collected and concentrated in vacuo to give 4.2 g of the title compound with purity high enough for subsequent use. 400 MHz 1H NMR (DMSO-d6) δ9.06 (s, 1H), 6.86 (t, 1H, J=7.8 Hz), 6.59 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.8 Hz), 2.75 (t, 2H, J=7.3 Hz), 2.67 (t, 2H, J=7.3 Hz), 1.92 (m, 2H). With zinc diiodide, sodium cyanoborohydride in diethyl ether, anhydrous dichloroethane Patent; Cheng, Xue-Min; Erasga, Noe; Filzen, Gary Frederick; Geyer, Andrew; Lee, Chitase; Trivedi, Bharat Kalidas; US2003/207916; (2003); (A1) English View in Reaxys 1.1 : Step 1. Step 1. Preparation of Indan-4-ol (Compound 1A) A mixture of 4-hydroxy-indan-1-one (5.0 g, 33.7 mmol), sodium cyanoborohydride (6.4 g, 101.1 mmol), and zinc iodide (32.3 g, 101.1 mmol) in dichloroethane, was heated at reflux for two hours. The reaction mixture was then filtered through 50 g SiO2 while still warm, eluding further with dichloroethane. The filtrate was collected and concentrated under vacuum. The residue was added to diethyl ether and the resulting white precipitate was filtered off. The filtrate was collected and concentrated in vacuo to give 4.2 g of the title compound with purity high enough for subsequent use. 400 MHz 1H NMR (DMSO-d6) δ 9.06 (s, 1H), 6.86 (t, 1H, J=7.8 Hz), 6.59 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.8 Hz), 2.75 (t, 2H, J=7.3 Hz), 2.67 (t, 2H, J=7.3 Hz), 1.92 (m, 2H). With zinc diiodide, sodium cyanoborohydride in diethyl ether, anhydrous dichloroethane Patent; Bratton, Larry D.; Cheng, Xue-Min; Erasga, Noe; Filzen, Gary F.; Geyer, Andrew G.; Lee, Chitase; Trivedi, Bharat K.; Unangst, Paul C.; US2004/209936; (2004); (A1) English View in Reaxys 12.1 : Step 1. Preparation of Indan-4-ol (Compound 12A) Step 1.Preparation of indan-4-ol (Compound 12A) A mixture of 4-hydroxy-indan-1-one (5.0 g, 33.7 mmol), sodium cyanoborohydride (6.4 g, 101.1 mmol), and zinc iodide (32.3 g, 101.1 mmol) in dichloroethane, was heated at reflux for two hours.The reaction mixture was then filtered through 50 g SiO2 while still warm, eluding further with dichloroethane.The filtrate was collected and concentrated under vacuum.The residue was added to diethyl ether and the resulting white precipitate was filtered off.The filtrate was collected and concentrated in vacuo to give 4.2 g of the title compound with purity high enough for subsequent use. 400 MHz 1H NMR (DMSO-d6) δ 9.06 (s, 1H), 6.86 (t, 1H, J=7.8 Hz), 6.59 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.8 Hz), 2.75 (t, 2H, J=7.3 Hz), 2.67 (t, 2H, J=7.3 Hz), 1.92 (m, 2H).
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With sodium cyanoborohydride, zinc(II) iodide in 1,2-dichloro-ethane, Time= 2h, Heating / reflux Patent; Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.; US2003/225158; (2003); (A1) English View in Reaxys 34-Hydroxy-2,3-dihydro-1H-inden-1-one
(W. Liu et al., Org. Lett. 2007, 9, 2915-2918) was reduced with sodium cyanoborohydride/trimethylsilyl chloride to provide 2,3-dihydro-1H-inden-4-ol. This was chlorinated with N-chlorosuccinimide to generate 7-chloro-2,3-dihydro-1H-inden-4-ol.
With chloro-trimethyl-silane, sodium cyanoborohydride Patent; Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O'Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan; US2012/252758; (2012); (A1) English View in Reaxys
OH
Rx-ID: 7245549 View in Reaxys 4/20 Yield
Conditions & References 4-Methoxy-indanol-(1) (XI), Li, fl. NH3, Ae. (neben 4-Methoxy-hydrinda-4,7-dien XII) Novak; Protiva; Collection of Czechoslovak Chemical Communications; vol. 23; (1958); p. 663,666, 671 View in Reaxys 4-Methoxy-inden (XIV), Li, fl. NH3, Ae. Novak; Protiva; Collection of Czechoslovak Chemical Communications; vol. 23; (1958); p. 663,666, 671 View in Reaxys 1) Dihydrocumarin, Al2O3, 170-180grad 2) Rk.prod. nach Clemmensen, Toluol Kraus; Bazant; Collection of Czechoslovak Chemical Communications; vol. 28; (1963); p. 1877,1878 View in Reaxys I, Isomerisierung Bruice et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 1673 View in Reaxys 2.b Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; LEE, Kuo-Hsiung; DONG, Yizhou; SHI, Qian; BASTOW, Kenneth, F.; WO2010/80414; (2010); (A2) English View in Reaxys
O
OH
Rx-ID: 28655714 View in Reaxys 5/20 Yield 95 %
Conditions & References With Blechert catalyst in dichloromethane, Time= 12h, T= 40 °C , Inert atmosphere Yoshida, Kazuhiro; Takahashi, Hidetoshi; Imamoto, Tsuneo; Chemistry - A European Journal; vol. 14; nb. 27; (2008); p. 8246 - 8261 View in Reaxys
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NH 2
OH
Rx-ID: 351208 View in Reaxys 6/20 Yield
Conditions & References With sulfuric acid, Diazotization.Erwaermen der Diazoniumsulfat-Loesung auf 50grad Goth; Chemische Berichte; vol. 61; (1928); p. 1460 View in Reaxys 2.1 :4-Aminoindan (3.0g) was added to a solution of concentrated sulphuric acid (2.4mL) in water (15mL). More water (15mL) was added and the mkture cooled to 5°C. A solution of sodium nitrite (1.7Ig) in water (4 JmL) was added portionwise to the mixture while maintaining the temperature below 5°C. After addition was complete the mixture was allowed to warm to room temperature and urea (0.29g) was added. The mixture was stirred for a further 5 minutes before being heated at 45°C for 30 minutes. The mixture was then cooled to room temperature and extracted with ethyl acetate. The combined organic extracts were washed with 2M aqueous sodium hydroxide (2x100mL) and these aqueous extracts were then acidified with hydrochloric acid and extracted with ethyl acetate (3x100mL). The combined organic extracts were then washed with brine and dried (Na2SO4) before being concentrated in vacuo. The resulting crude product was chromatographed over silica gel. Elution with ethyl acetate/hexanes (1:7) gave 4hydroxyindan as an orange oil (1.0g). Stage 1: With sulfuric acid, urea, sodium nitrite in water, Time= 0.583333h, T= 5 - 45 °C , Heating / reflux Stage 2: in water Patent; BIOTRON LIMITED; WO2006/135978; (2006); (A1) English View in Reaxys
O
OH
HN OH
O
OH
Rx-ID: 10189187 View in Reaxys 7/20 Yield
Conditions & References
880 mg, 210 mg
With sodium cyanoborohydride in methanol, Time= 4h, Heating Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys
OH
NH 2
OH
Rx-ID: 10215459 View in Reaxys 8/20 Yield 110 mg
Conditions & References With formaldehyd, sodium cyanoborohydride in acetonitrile, Time= 5h, Heating Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys Reaction Steps: 2 1: toluene 2: 210 mg / NaCNBH3 / methanol / 4 h / Heating With sodium cyanoborohydride in methanol, toluene Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140
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View in Reaxys
OH
O
OH
Rx-ID: 12453247 View in Reaxys 9/20 Yield 90%
Conditions & References 26 : Tetra-n-propyl 2-6-tert-butyl-7-hydroxy-4-indanyl]ethenylidene-1,1-diphosphonate EXAMPLE 26 Tetra-n-propyl 2-6-tert-butyl-7-hydroxy-4-indanyl]ethenylidene-1,1-diphosphonate To a solution of 7-hydroxyindan-1-one (6.0 g, 40 mmole) in trifluoroacetic acid (30 ml), triethylsilane (10.23 g, 87.9 mmole) was added. The mixture was refluxed for 5 hours, poured into water (200 ml) and extracted with diethyl ether (2*200 ml). The extract was washed with water. The ethereal solution was extracted with 4NNaOH (3*50 ml). The alkaline extract was washed with diethyl ether then acidified to pH1 with hydrochloric acid. The aqueous mixture was extracted with diethyl ether and the ethereal extract was washed with water and aqueous saturated sodium chloride, was dried, and the solvents evaporated to give 4-hydroxyindane as a colourless oil (4.9 g, 90percent). With triethylsilane in trifluoroacetic acid Patent; Symphar S.A.; US5204336; (1993); (A1) English View in Reaxys
90%
26 : Tetra-n-propyl 2-[6-tert-butyl-7-hydroxy-4-indanyl]ethenylidene-1,1-diphosphonate. Example 26 Tetra-n-propyl 2-[6-tert-butyl-7-hydroxy-4-indanyl]ethenylidene-1,1-diphosphonate. To a solution of 7-hydroxyindan-1-one (6.0 g, 40 mmole) in trifluoroacetic acid (30 ml), triethylsilane (10.23 g, 87.9 mmole) was added. The mixture was refluxed for 5 hours, poured into water (200 ml) and extracted with diethyl ether (2 x 200 ml). The extract was washed with water. The ethereal solution was extracted with 4NNaOH (3 x 50 ml). The alkaline extract was washed with diethyl ether then acidified to PH1 with hydrochloric acid. The aqueous mixture was extracted with diethyl ether and the ethereal extract was washed with water and aqueous saturated sodium chloride, was dried, and the solvents evaporated to give 4-hydroxyindane as a colourless oil (4.9 g, 90percent). With triethylsilane in trifluoroacetic acid Patent; SYMPHAR S.A.; EP418064; (1991); (A2) English View in Reaxys Reaction Steps: 2 1: NaCNBH3; ammonium acetate 2: 110 mg / NaCNBH3; paraformaldehyde / acetonitrile / 5 h / Heating With ammonium acetate, formaldehyd, sodium cyanoborohydride in acetonitrile Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys Reaction Steps: 3 1: NaCNBH3; ammonium acetate 2: toluene 3: 210 mg / NaCNBH3 / methanol / 4 h / Heating With ammonium acetate, sodium cyanoborohydride in methanol, toluene Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys
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Reaction Steps: 3 1: NH2OH 2: H2 3: 110 mg / NaCNBH3; paraformaldehyde / acetonitrile / 5 h / Heating With formaldehyd, hydrogen, hydroxylamine, sodium cyanoborohydride in acetonitrile Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys Reaction Steps: 4 1: NH2OH 2: H2 3: toluene 4: 210 mg / NaCNBH3 / methanol / 4 h / Heating With hydrogen, hydroxylamine, sodium cyanoborohydride in methanol, toluene Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys
OH
N
OH
OH
Rx-ID: 12457884 View in Reaxys 10/20 Yield
Conditions & References Reaction Steps: 2 1: H2 2: 110 mg / NaCNBH3; paraformaldehyde / acetonitrile / 5 h / Heating With formaldehyd, hydrogen, sodium cyanoborohydride in acetonitrile Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys Reaction Steps: 3 1: H2 2: toluene 3: 210 mg / NaCNBH3 / methanol / 4 h / Heating With hydrogen, sodium cyanoborohydride in methanol, toluene Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140 View in Reaxys
OH
Rx-ID: 9890576 View in Reaxys 11/20 Yield 77 %
Conditions & References With [(tris(1-pyrazolyl)borate)Ru(P(phenyl)3)(CH3CN)2]PF6, water in various solvent(s), Time= 24h, T= 100 °C Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412 View in Reaxys
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Si S
O
O
OH
S
Rx-ID: 2556288 View in Reaxys 12/20 Yield
Conditions & References
11 %, 17 % With Me2S(SMe)BF4 in dichloromethane, Time= 20h, Ambient temperature Dieter; Lin; Journal of Organic Chemistry; vol. 49; nb. 17; (1984); p. 3183 - 3195 View in Reaxys
O
OH
Rx-ID: 1058940 View in Reaxys 13/20 Yield
Conditions & References With pyrrolidine in water, T= 30 °C , other catalysts, Rate constant Becker,A.R. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5058 - 5068 View in Reaxys
OH
O
Rx-ID: 1061662 View in Reaxys 14/20 Yield
Conditions & References With formic acid, dihydrogen peroxide Dallacker,F.; Van Werst,J.; Chemische Berichte; vol. 105; (1972); p. 2565 - 2574 View in Reaxys
OH
Rx-ID: 22732974 View in Reaxys 15/20 Yield
Conditions & References Reaction Steps: 4 1: AlCl3 2: AlCl3 3: AlCl3 / toluene / Ambient temperature 4: HCO2H, aq. H2O2 With aluminium trichloride, formic acid, dihydrogen peroxide in toluene Dallacker,F.; Van Werst,J.; Chemische Berichte; vol. 105; (1972); p. 2565 - 2574 View in Reaxys O
OH
Rx-ID: 22734429 View in Reaxys 16/20
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Yield
Conditions & References Reaction Steps: 2 1: AlCl3 / toluene / Ambient temperature 2: HCO2H, aq. H2O2 With aluminium trichloride, formic acid, dihydrogen peroxide in toluene Dallacker,F.; Van Werst,J.; Chemische Berichte; vol. 105; (1972); p. 2565 - 2574 View in Reaxys
OH
Rx-ID: 22739001 View in Reaxys 17/20 Yield
Conditions & References Reaction Steps: 3 1: AlCl3 2: AlCl3 / toluene / Ambient temperature 3: HCO2H, aq. H2O2 With aluminium trichloride, formic acid, dihydrogen peroxide in toluene Dallacker,F.; Van Werst,J.; Chemische Berichte; vol. 105; (1972); p. 2565 - 2574 View in Reaxys
sodium-<indan sulfonate-(4)> OH
Rx-ID: 7245550 View in Reaxys 18/20 Yield
Conditions & References With potassium hydroxide Arnold; Zaugg; Journal of the American Chemical Society; vol. 63; (1941); p. 1317,1318 View in Reaxys
4-iodo-indan NH 2
OH
Rx-ID: 7444232 View in Reaxys 19/20 Yield
Conditions & References With sulfuric acid, sodium nitrite, Diazotization.Behandlung der erhaltenen Diazoniumsalz-Loesung mit KI, zuletzt bei Siedetemperatur Arnold; Zaugg; Journal of the American Chemical Society; vol. 63; (1941); p. 1317,1318 View in Reaxys
sodium salt of/the/ hydrindene-sulfonic acid-(4) OH
Rx-ID: 7245551 View in Reaxys 20/20 Yield
Conditions & References durch Kalischmelze Moschner; Chemische Berichte; vol. 34; (1901); p. 1259 View in Reaxys
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