4-Indanol (2,3-Dihydro-1H-inden-4-ol) by Asch

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References A

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Stage #1: With 2,3-benzodioxin-1,4-dione

Heating; Stage #2: With sodium hydrogencarbonate in methanol; water

12 h; Inert atmosphere; Overall yield = 53 percent; Hide Experimental Procedure

Rx-ID: 38785279 Find similar reactions

BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; AXELROD, Abram; JOHNSON, Trevor, C.; SIEGEL, Dionicio; CAMELIO, Andrew, M.; YUAN, Changxia; ELIASEN, Anders

Patent: WO2014/158209 A1, 2014 ; Location in patent: Page/Page column 9; 10 ; Title/Abstract Full Text Show Details

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. A

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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; Hide Experimental Procedure

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Yuan, Changxia; Liang, Yong; Hernandez, Taylor; Berriochoa, Adrian; Houk, Kendall N.; Siegel, Dionicio

Nature, 2013 , vol. 499, # 7457 p. 192 - 196 Title/Abstract Full Text View citing articles Show Details

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.

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With sodium cyanoborohydride; zinc(II) iodide in anhydrous dichloroethane

2 h; Reflux; Hide Experimental Procedure

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Rx-ID: 11169853 Find similar reactions

InterMune, Inc.

Patent: US2011/152246 A1, 2011 ; Location in patent: Page/Page column 118-119 ; Title/Abstract Full Text Show Details

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 dichloroethane (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 IIIIb (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). 42%

With sodium cyanoborohydride; zinc(II) iodide in 1,2-dichloro-ethane

2 h; 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, 2007 , vol. 17, # 16 p. 4625 - 4629 Title/Abstract Full Text View citing articles Show Details

With zinc diiodide; sodium cyanoborohydride in diethyl ether; anhydrous dichloroethane

Cheng, Xue-Min; Erasga, Noe; Filzen, Gary Frederick; Geyer, Andrew; Lee, Chitase; Trivedi, Bharat Kalidas

Patent: US2003/207916 A1, 2003 ;

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Title/Abstract Full Text Show Details

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

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Bratton, Larry D.; Cheng, Xue-Min; Erasga, Noe; Filzen, Gary F.; Geyer, Andrew G.; Lee, Chitase; Trivedi, Bharat K.; Unangst, Paul C.

Patent: US2004/209936 A1, 2004 ; Title/Abstract Full Text Show Details

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 sodium cyanoborohydride; zinc(II) iodide in 1,2-dichloro-ethane

2 h; Heating / reflux; Hide Experimental Procedure

Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.

Patent: US2003/225158 A1, 2003 ; Location in patent: Page 29 ; Title/Abstract Full Text Show Details

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). With chloro-trimethyl-silane; sodium cyanoborohydride

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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

Patent: US2012/252758 A1, 2012 ; Location in patent: Page/Page column 69 ; Title/Abstract Full Text Show Details

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 Nchlorosuccinimide to generate 7-chloro-2,3-dihydro-1H-inden-4-ol.

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Rx-ID: 7245549 Find similar reactions

4-Methoxy-indanol-(1) (XI), Li, fl. NH3, Ae. (neben 4-Methoxy-hydrinda-4,7-dien XII);

4-Methoxy-inden (XIV), Li, fl. NH3, Ae.;

Novak; Protiva

Collection of Czechoslovak Chemical Communications, 1958 , vol. 23, p. 663,666, 671 Full Text View citing articles Show Details

Novak; Protiva

Collection of Czechoslovak Chemical Communications, 1958 , vol. 23, p. 663,666, 671 Full Text View citing articles Show Details

1) Dihydrocumarin, Al2O3, 170-180grad 2) Rk.prod. nach Clemmensen, Toluol;

Kraus; Bazant

Collection of Czechoslovak Chemical Communications, 1963 , vol. 28, p. 1877,1878 Full Text Show Details

I, Isomerisierung;

Bruice et al.

Journal of the American Chemical Society, 1973 , vol. 95, p. 1673 Full Text View citing articles Show Details

THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; LEE, Kuo-Hsiung; DONG, Yizhou; SHI, Qian; BASTOW, Kenneth, F.

Patent: WO2010/80414 A2, 2010 ; Location in patent: Page/Page column 29 ; Title/Abstract Full Text Show Details

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With Blechert catalyst in dichloromethane

T=40°C; 12 h; Inert atmosphere;

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Rx-ID: 28655714 Find similar reactions

Yoshida, Kazuhiro; Takahashi, Hidetoshi; Imamoto, Tsuneo

Chemistry - A European Journal, 2008 , vol. 14, # 27 p. 8246 - 8261 Title/Abstract Full Text View citing articles Show Details

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Diazotization.Erwaermen der DiazoniumsulfatLoesung auf 50grad;

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Rx-ID: 351208 Find similar reactions

Goth

Chemische Berichte, 1928 , vol. 61, p. 1460 Full Text View citing articles Show Details

Stage #1: With sulfuric acid; urea; sodium nitrite in water

T=5 - 45°C; 0.583333 h; Heating / reflux; Stage #2: in water

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BIOTRON LIMITED

Patent: WO2006/135978 A1, 2006 ; Location in patent: Page/Page column 24 ; Title/Abstract Full Text Show Details

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 4- hydroxyindan as an orange oil (1.0g). A

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Rx-ID: 10189187 Find similar reactions

A: 880 mg B: 210 mg

With sodium cyanoborohydride in methanol

4 h; Heating;

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10215459 Find similar reactions

With formaldehyd; sodium cyanoborohydride in acetonitrile

5 h; Heating;

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: toluene 2: 210 mg / NaCNBH3 / methanol / 4 h / Heating View Scheme

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

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With triethylsilane in trifluoroacetic acid

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Rx-ID: 12453247 Find similar reactions

Symphar S.A.

Patent: US5204336 A1, 1993 ; Title/Abstract Full Text Show Details

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). 90%

With triethylsilane in trifluoroacetic acid

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SYMPHAR S.A.

Patent: EP418064 A2, 1991 ; Title/Abstract Full Text Show Details

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). Multi-step reaction with 2 steps 1: NaCNBH3; ammonium acetate 2: 110 mg / NaCNBH3; paraformaldehyde / acetonitrile / 5 h / Heating View Scheme

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: NaCNBH3; ammonium acetate 2: toluene 3: 210 mg / NaCNBH3 / methanol / 4 h / Heating View Scheme

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: NH2OH 2: H2

3: 110 mg / NaCNBH3; paraformaldehyde / acetonitrile / 5 h / Heating View Scheme

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 4 steps 1: NH2OH 2: H2

3: toluene 4: 210 mg / NaCNBH3 / methanol / 4 h / Heating View Scheme

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12457884 Find similar reactions

Multi-step reaction with 2 steps 1: H2

2: 110 mg / NaCNBH3; paraformaldehyde / acetonitrile / 5 h / Heating View Scheme

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: H2

2: toluene 3: 210 mg / NaCNBH3 / methanol / 4 h / Heating View Scheme

Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham

Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140 Title/Abstract Full Text View citing articles Show Details

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With [(tris(1-pyrazolyl)borate)Ru(P(phenyl)3) (CH3CN)2]PF6; water in various solvent(s) T=100°C; 24 h;

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Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung

Journal of the American Chemical Society, 2005 , vol. 127, # 10 p. 3406 - 3412 Title/Abstract Full Text View citing articles Show Details

Rx-ID: 9890576 Find similar reactions

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A: 17% B: 11%

With Me2S(SMe)BF4 in dichloromethane

20 h; Ambient temperature;

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Dieter; Lin

Journal of Organic Chemistry, 1984 , vol. 49, # 17 p. 3183 - 3195 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With pyrrolidine in water

T=30°C; other catalysts; Rate constant;

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Rx-ID: 1058940 Find similar reactions

Becker,A.R. et al.

Journal of the American Chemical Society, 1977 , vol. 99, p. 5058 - 5068 Full Text View citing articles Show Details

Synthesize Find similar With formic acid; dihydrogen peroxide

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Rx-ID: 1061662 Find similar reactions

Dallacker,F.; Van Werst,J.

Chemische Berichte, 1972 , vol. 105, p. 2565 - 2574 Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: AlCl3

2: AlCl3

3: AlCl3 / toluene / Ambient temperature 4: HCO2H, aq. H2O2

View Scheme

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Rx-ID: 22732974 Find similar reactions

Dallacker,F.; Van Werst,J.

Chemische Berichte, 1972 , vol. 105, p. 2565 - 2574 Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: AlCl3 / toluene / Ambient temperature 2: HCO2H, aq. H2O2

View Scheme

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Rx-ID: 22734429 Find similar reactions

Dallacker,F.; Van Werst,J.

Chemische Berichte, 1972 , vol. 105, p. 2565 - 2574 Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: AlCl3

2: AlCl3 / toluene / Ambient temperature 3: HCO2H, aq. H2O2

View Scheme

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Rx-ID: 22739001 Find similar reactions

Dallacker,F.; Van Werst,J.

Chemische Berichte, 1972 , vol. 105, p. 2565 - 2574 Full Text View citing articles Show Details

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Rx-ID: 7245550 Find similar reactions

Arnold; Zaugg

Journal of the American Chemical Society, 1941 , vol. 63, p. 1317,1318 Full Text View citing articles Show Details

Synthesize Find similar With sulfuric acid; sodium nitrite

Diazotization.Behandlung der erhaltenen Diazoniumsalz-Loesung mit KI, zuletzt bei Siedetemperatur;

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Rx-ID: 7444232 Find similar reactions

Arnold; Zaugg

Journal of the American Chemical Society, 1941 , vol. 63, p. 1317,1318 Full Text View citing articles Show Details

Synthesize Find similar durch Kalischmelze;

Rx-ID: 7245551 Find similar reactions

Moschner

Chemische Berichte, 1901 , vol. 34, p. 1259 Full Text View citing articles Show Details