2-Hydroxy-5-methoxybenzaldehyde by Asch

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PubChem

eMolecules

Reactions (32)

Yield

Substances (6)

Citations (67)

Conditions

References

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Rx-ID: 664705 Find similar reactions

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72%

With sodium hydroxide in water

1 h; Heating;

Chu, Kwong Yung; Griffiths, John; Ward, David

Journal of Chemical Research, Miniprint, 1981 , # 10 p. 3701 - 3721 Title/Abstract Full Text Show Details

65%

With sodium hydroxide

Reimer-Tiemann reaction; Heating;

Harmata; Wu; Kahraman; Welch

Synthetic Communications, 2001 , vol. 31, # 21 p. 3345 - 3359 Title/Abstract Full Text View citing articles Show Details

48%

With sodium hydroxide

T=70 - 80°C; 0.5 h;

Baker, Raymond; Castro, Jose L.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , # 1 p. 47 - 65 Title/Abstract Full Text View citing articles Show Details

23 %

With sodium hydroxide

Cochran, John C.; Melville, Margaret G.

Spectr.

23 % Spectr.

5 h; Irradiationother p-substituted phenols, var. amount of water and time of sonication; Product distribution;

Synthetic Communications, 1990 , vol. 20, # 4 p. 609 - 616 Title/Abstract Full Text Show Details

With sodium hydroxide

Tiemann; Mueller

Chemische Berichte, 1881 , vol. 14, p. 1986 Full Text Show Details

With sodium hydroxide

T=70°C;

Gillespie

Biochemical Preparations, 1953 , vol. 3, p. 79,81 Full Text Show Details

With sodium hydroxide

Kappe Th.; Witoszynskyj Th.

Archiv der Pharmazie, 1975 , vol. 308, # 5 p. 339 - 346 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide

5 h; Irradiation;

Cochran, John C.; Melville, Margaret G.

Synthetic Communications, 1990 , vol. 20, # 4 p. 609 - 616 Title/Abstract Full Text Show Details

With sodium hydroxide

Reimer-Tiemann reaction; 4 h; Heating;

Majumdar; Chattopadhyay; Sinha

Tetrahedron Letters, 2008 , vol. 49, # 8 p. 1319 - 1322 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in ethanol; water

1 h; Heating;

Lai, Guoyin; Wang, Sujing; Wang, Zhiyong

Tetrahedron Asymmetry, 2008 , vol. 19, # 15 p. 1813 - 1819 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

Reimer-Tiemann reaction; Heating;

Majumdar, Krishna C.; Chattopadhyay, Buddhadeb; Sinha, Biswajit

Synthesis, 2008 , # 23 art. no. Z18408SS, p. 3857 - 3863 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

Reimer-Tiemann reaction; 4 h; Reflux;

Majumdar; Ansary, Inul; Sinha, Biswajit; Chattopadhyay, Buddhadeb

Synthesis, 2009 , # 21 p. 3593 - 3602 Title/Abstract Full Text View citing articles Show Details

in polyethylene glycol-400

Reimer-Tiemann reaction; Alkaline conditionsPhase-transfer conditions;

Reddy, S. Satyanarayana; Krupadanam, G. L. David

Synthetic Communications, 2010 , vol. 40, # 9 p. 1305 - 1311 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

Reflux;

Foroumadi, Alireza; Emami, Saeed; Sorkhi, Maedeh; Nakhjiri, Maryam; Nazarian, Zohreh; Heydari, Samaneh; Ardestani, Sussan K.; Poorrajab, Fatemeh; Shafiee, Abbas

Chemical Biology and Drug Design, 2010 , vol. 75, # 6 p. 590 - 596 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide

Reimer-Tiemann Phenol Formylation; 2 h; Reflux; Hide Experimental Procedure

Boukharsa, Youness; Meddah, Bouchra; Tiendrebeogo, Ramata Yvette; Ibrahimi, Azeddine; Taoufik, Jamal; Cherrah, Yahia; Benomar, Ali; Faouzi, My El Abbes; Ansar, M'Hammed

Medicinal Chemistry Research, 2016 , vol. 25, # 3 p. 494 - 500 Title/Abstract Full Text View citing articles Show Details

General procedures for the formylation of phenols 2a–g: Method A

General procedure: A solution of the substituted phenols 1 (0.5 mol) in300 mL of 10 N NaOH (3 mol) was heated to 65 °C. Then80 mL of CHCl3 was added in three portions over 15 min.The mixture was heated at reflux in chloroform for 2 h.After cooling, the mixture was acidified to pH 1 with 12 NHCl, the organic layer collected and the aqueous layerextracted with chloroform. The combined chloroformsolution was dried and evaporated to give a crude productwhich was distilled or recrystallized from an appropriatesolvent.

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100%

Stage #1: formaldehyd With triethylamine; magnesium chloride in tetrahydrofuran

T=20°C; 0.166667 h; Inert atmosphereReflux; Stage #2: 4-methoxy-phenol in tetrahydrofuran

Reflux;

Fugard, Alison J.; Thompson, Bethany K.; Slawin, Alexandra M. Z.; Taylor, James E.; Smith, Andrew D.

Organic Letters, 2015 , vol. 17, # 23 p. 5824 - 5827 Title/Abstract Full Text View citing articles Show Details

100%

Stage #1: formaldehyd With triethylamine; magnesium chloride in tetrahydrofuran

T=20 - 25°C; 0.166667 h; Stage #2: 4-methoxy-phenol in tetrahydrofuran

Reflux;

Barrios Antúnez, Diego-Javier; Greenhalgh, Mark D.; Fallan, Charlene; Slawin, Alexandra M. Z.; Smith, Andrew D.

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 30 p. 7268 - 7274 Title/Abstract Full Text View citing articles Show Details

97%

With triethylamine; magnesium chloride in acetonitrile

2 h; Heating;

Hofslokken, Nini U.; Skattebol, Lars

Acta Chemica Scandinavica, 1999 , vol. 53, # 4 p. 258 - 262 Title/Abstract Full Text View citing articles Show Details

91%

With triethylamine; magnesium chloride in acetonitrile

8 h; Heating / reflux; Hide Experimental Procedure

VERSITECH LIMITED; MORNINGSIDE VENTURES LIMITED

Patent: WO2008/110063 A1, 2008 ; Location in patent: Page/Page column 31 ; Title/Abstract Full Text Show Details

Synthesis of 2-hydroxy-5-methoxybenzaldehyde; [104] To a mixture of compound p-methoxyphenol (3 g, 24.2 mmol), anhydrous magnesium dichloride (3.48 g, 37.0 mmol) and dry triethylamine (12.8 mL, 92.1 mmol) in 100 mL of acetonitrile was added dry paraformaldehyde (5 g, 167 mmol). The reaction mixture was refluxed for 8 hours and cooled down to room temperature. Then the reaction mixture was poured into 5percent HCl (300 mL) and extracted with diethyl ether (200 mL) for three times. The combined organic layers were dried over anhydrous Na2SO4, filtered, and evaporated. The residue was purified by flash column chromatography (20percent EtOAc in n-hexane) to yield 3.35 g of 2-hydroxy-5-methoxybenzaldehyde (91percent yield). 91%

With triethylamine; magnesium chloride in acetonitrile

8 h; RefluxInert atmosphere;

Sun, Zhen-Ning; Liu, Feng-Qin; Chen, Yan; Tam, Paul Kwong Hang; Yang, Dan

Organic Letters, 2008 , vol. 10, # 11 p. 2171 - 2174 Title/Abstract Full Text View citing articles Show Details

90%

With magnesium methanolate in toluene

T=90°C;

Quesada, Ernesto; Stockley, Martin; Ragot, Jacques P; Prime, Michael E; Whitwood, Adrian C; Taylor, Richard J K

Organic and biomolecular chemistry, 2004 , vol. 2, # 17 p. 2483 - 2495 Title/Abstract Full Text View citing articles Show Details

90%

Stage #1: 4-methoxy-phenol With magnesium methanolate

T=20°C; 0.0166667 h; Stage #2: formaldehyd T=20°C; 0.166667 h; Stage #3: With sulfuric acid

T=20°C; 0.166667 h; regioselective reaction; Hide Experimental Procedure

Balali, Ebrahim; Shameli, Abolghasem; Naeimi, Hoseein; MehdiGhanbari, Mohammad

Oriental Journal of Chemistry, 2013 , vol. 29, # 4 p. 1611 - 1614 Title/Abstract Full Text View citing articles Show Details

General procedure: A aromatic Phenol 1 (0.1 mol), magnesiummethoxide (5 gr ), and the mixture was grindingto 1 minute at room temperature. A slurry ofparaformaldehyde powder6 (4 gr) in under grindingwas added in small portions over 2 min to thereaction mixture. Stirring was continued at r.t for 8min, after which added slowly to 10percent sulfuric acid(20 ml g). The resulting mixture was stirred for 10min, after which the aqueous layer was separatedand extracted with ethyl acetate (2 × 100 ml). Thecombined organic layers and extracts were washedwith 10percent sulfuric acid (20 ml) and water (20 ml)and evaporated under reduced pressure to give thesalicyaldehyde 3. 74%

Stage #1: With triethylamine; magnesium chloride in acetonitrile

T=45°C; 3 h; Heating / reflux; Stage #2: With hydrogenchloride in water; acetonitrile

Shanks, Thomas Elbert; Maleski, Robert Joseph

Patent: US2003/199714 A1, 2003 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

Hide Experimental Procedure

A mixture of 600 g of acetonitrile, 186.2 g of 4-methoxyphenol (1.5 moles) and 214 g (2.25 moles) of anhydrous magnesium chloride was warmed to 45° C. and 227.4 g (2.25 moles) of triethylamine was added dropwise at that temperature. Paraformaldehyde (150 g, 4.75 moles) was then added and the reaction was heated to reflux. Methanol was removed over 3 hours by distillation, using a 10-inch column packed with Penn-State packing. The weight of the methanol removed (vapor temperature 60-65° C.) was 130 g. The solution was cooled to 60° C. and added to 900 mL of water. The solution was acidified with 240 mL of conc. HCl and extracted with 150 g of ethyl acetate. The ethyl acetate solution was washed once with 300 mL of tap water, clarified through diatomaceous earth, and stripped on a rotary evaporator at 10 mm pressure and 85° C. bath temperature. The weight of the product was 206.5 g, the liquid chromatograph area percent was 86percent, and liquid chromatograph weight percent was 82percent. The overall assay yield was 74percent 52%

With triethylamine; magnesium chloride in acetonitrile

8 h; Inert atmosphereReflux;

Hu, Jun Jacob; Wong, Nai-Kei; Gu, Qiangshuai; Bai, Xiaoyu; Ye, Sen; Yang, Dan

Organic Letters, 2014 , vol. 16, # 13 p. 3544 - 3547 Title/Abstract Full Text View citing articles Show Details

With tributyl-amine; tin(IV) chloride

1.) toluene, room temperature, 20 min, 2.) 100 deg C, 8 h; Yield given. Multistep reaction;

Casiraghi, Giovanni; Casnati, Giuseppe; Puglia, Giuseppe; Sartori, Giovanni; Terenghi, Giuliana

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1862 - 1865 Title/Abstract Full Text View citing articles Show Details

With magnesium methanolate

1.) MeOH, toluene, reflux, 2.) 95 deg C, 1 h; 30-40 deg C, 2 h; Yield given. Multistep reaction;

Aldred, Robert; Johnston, Robert; Levin, Daniel; Neilan, James

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 13 p. 1823 - 1832 Title/Abstract Full Text View citing articles Show Details

With magnesium methanolate in toluene

T=90°C;

Quesada, Ernesto; Stockley, Martin; Taylor, Richard J. K.

Tetrahedron Letters, 2004 , vol. 45, # 25 p. 4877 - 4881 Title/Abstract Full Text View citing articles Show Details

Stage #1: 4-methoxy-phenol With magnesium methanolate in methanol

McGarrigle; Murphy; Gilheany

Tetrahedron Asymmetry, 2004 , vol. 15, # 8 p. 1343 - 1354 Title/Abstract Full Text View citing articles Show Details

Stage #2: formaldehyd in methanol; toluene

T=80°C; 2 h; Stage #3: With sulfuric acid in methanol; toluene

T=50°C; 2 h;

With triethylamine; magnesium chloride

Sessions, E. Hampton; Smolinski, Michael; Wang, Bo; Frackowiak, Bozena; Chowdhury, Sarwat; Yin, Yan; Chen, Yen Ting; Ruiz, Claudia; Lin, Li; Pocas, Jennifer; Schroeter, Thomas; Cameron, Michael D.; LoGrasso, Philip; Feng, Yangbo; Bannister, Thomas D.

Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 6 p. 1939 - 1943 Title/Abstract Full Text View citing articles Show Details

With triethylamine; magnesium chloride in acetonitrile

8 h; Reflux; Hide Experimental Procedure

Liu, Qingchuan; Wen, Ke; Zhang, Zhenfeng; Wu, Zhengxing; Zhang, Yong Jian; Zhang, Wanbin

Tetrahedron, 2012 , vol. 68, # 26 p. 5209 - 5215 Title/Abstract Full Text View citing articles Show Details

4.2.2.2. 4-Methyl-2-[(3-methyl)-3-pentenyl]phenol (1b)

General procedure: To a solution of phenol 3b (2.6 g, 24.0 mmol), anhydrous MgCl2 (3.5 g, 36.8 mmol), and paraformaldehyde (5.0 g, 166.5 mmol) in MeCN (100 ml) was added triethylamine (12.8 ml, 91.8 mmol). The reaction mixture was heated under reflux conditions for 8 h. Hydrochloric acid (5percent) was added and the mixture extracted with ether and dried over Na2SO4. Solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography to give the intermediate 4b (2.8 g, 86percent yield).

Stage #1: 4-methoxy-phenol With magnesium methanolate in methanol

Mattsson, Cecilia; Svensson, Peder; Sonesson, Clas

European Journal of Medicinal Chemistry, 2014 , vol. 73, p. 177 - 186 Title/Abstract Full Text View citing articles Show Details

Stage #2: formaldehyd in toluene

Stage #3: With hydrogenchloride in water

2.3 g

With triethylamine; magnesium chloride in acetonitrile

8 h; Reflux; Hide Experimental Procedure

Shanghai Tangrun Pharmaceuticals, Co. Ltd; ZHANG, Suo ming

Patent: EP2740734 A1, 2014 ; Location in patent: Paragraph 0040 ; Title/Abstract Full Text Show Details

4.S4A:Step S4A: Synthesis of 2-hydroxy-5-methoxy-benzaldehyde (4A) Step S4A: Synthesis of 2-hydroxy-5-methoxy-benzaldehyde (4A) To a mixture of MgCl2 (3.48g, 37.0mmol), TEA (12.8mL, 92.1 mmol) and paraformaldehyde (5g, 167mmol) in MeCN (100mL) was added 4-methoxy-phenol (3g, 24.2mmol). The mixture was refluxed for 8 hours, cooled to room temperature, then poured into 5percent HCl (300mL), extracted with ethyl acetate (200mL*3). The combined organic layer was dried, concentrated and purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/5) to give 2.3g of 2-hydroxy-5-methoxy-benzaldehyde (4A). 1H-NMR (DMSO-d6) : δ (ppm): 10.67 (s, 1H), 9.87 (s, 1H), 7.18 (dd, J1 = 8.8

Hz, J2 = 3.6 Hz, 1H), 7.02 (d, J = 2.8 Hz, 1H), 6.95 (d, J = 8.8 Hz, 1H), 3.83 (s, 3H). MS (ESI): M++1=153.15. 2.3 g

With triethylamine; magnesium chloride in acetonitrile

8 h; Reflux; Hide Experimental Procedure

Shanghai Tangrun Pharmaceuticals, Co., Ltd.; Zhang, Suoming

Patent: US2014/163219 A1, 2014 ; Location in patent: Paragraph 0105-0107 ; Title/Abstract Full Text Show Details

4.s.4A:Step S4A: Synthesis of 2-hydroxy-5-methoxy-benzaldehyde (4A) Step S4A: Synthesis of 2-hydroxy-5-methoxy-benzaldehyde (4A) To a mixture of MgCl2 (3.48 g, 37.0 mmol), TEA (12.8 mL, 92.1 mmol) and paraformaldehyde (5 g, 167 mmol) in MeCN (100 mL) was added 4-methoxy-phenol (3 g, 24.2 mmol). The mixture was refluxed for 8 hours, cooled to room temperature, then poured into 5percent HCl (300 mL), extracted with ethyl acetate (200 mL*3). The combined organic layer was dried, concentrated and purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/5) to give 2.3 g of 2-hydroxy-5-methoxy-benzaldehyde (4A). 1H-NMR (DMSO-d ): δ (ppm): 10.67 (s, 1H), 9.87 (s, 1H), 7.18 (dd, J1=8.8 Hz, J2=3.6 Hz, 1H), 7.02 (d, J=2.8 Hz, 1H), 6.95 (d, J=8.8 Hz, 1H), 3.83 (s, 3H). MS (ESI): M++1=153.15. 6 With triethylamine; magnesium chloride in tetrahydrofuran

T=80°C; 8 h;

Nakai, Yuhta; Moriyama, Katsuhiko; Togo, Hideo

European Journal of Organic Chemistry, 2014 , vol. 2014, # 27 p. 6077 - 6083 Title/Abstract Full Text View citing articles Show Details

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With aluminum (III) chloride in dichloromethane

T=20°C; 12 h; Inert atmosphere; Hide Experimental Procedure

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Rx-ID: 4576798 Find similar reactions

SALK INSTITUTE FOR BIOLOGICAL STUDIES; MITOKYNE, INC.; EVANS, Ronald; BAIGA, Thomas, J.; BOCK, Mark, G.; DOWNES, Michael; EMBLER, Emi, Kanakubo; FAN, Weiwei; KEANA, John, F.W.; KLUGE, Arthur, F.; NOEL, Joseph, P.; PATANE, Mike, A.

Patent: WO2014/165827 A1, 2014 ; Location in patent: Page/Page column 133; 134 ; Title/Abstract Full Text Show Details

28.a:Synthesis of 2-hydroxy-5-methoxybenzaldehyde In a 250-mL round bottom flask, a stirred solution of 2,5-dimethoxybenzaldehyde (5.0 g, 30.02 mmol) was dissolved in DCM (50 mL). Aluminum chloride (18.2 g, 136.8 mmol) was added to the above solution at rt under nitrogen atmosphere. The reaction mixture was stirred at rt for 12 h. Upon completion of the reaction (TLC), the reaction mixture was diluted with cold water and extracted with DCM (100 mL x 2). The combined organic extract was washed with brine and concentrated under reduced pressure to get title compound (4.51 g, 98percent) as yellow oil. LCMS (m/: 152.1 (M+l)+.

98%

With aluminum (III) chloride in dichloromethane

T=20°C; 12 h; Inert atmosphere; Hide Experimental Procedure

SALK INSTITUTE FOR BIOLOGICAL STUDIES; EVANS, Ronald, M.; DOWNES, Michael

Patent: WO2016/57322 A1, 2016 ; Location in patent: Page/Page column 167 ; Title/Abstract Full Text Show Details

28.a:a) Synthesis of 2-hydroxy-5-methoxybenzaldehyde In a 250-mL round bottom flask, a stuffed solution of 2,5-dimethoxybenzaldehyde (5.0 g, 30.02 mmol) was dissolved in DCM (50 rnL). Aluminum chloride (18.2 g. 136.8 rnrnol) was added to the above solution at rt under nitrogen atmosphere. The reaction mixture was stirred at r for 12 h. Upon completion of the reaction (TLC), the reaction mixture was diluted with cold water and extracted with DCM (100 mL x 2).The combined organic extract was washed with brine and concentrated under reduced pressure to get titlecompound (4.51 g, 98percent) as yellow oil. LCMS (m/z): 152.1 (M+1). 95%

With beryllium(II) chloride in toluene

7 h;

Sharghi, Hashem; Tamaddon, Fatemeh

Tetrahedron, 1996 , vol. 52, # 43 p. 13623 - 13640 Title/Abstract Full Text View citing articles Show Details

Stage #1: With aluminum (III) chloride in dichloromethane

T=0 - 20°C; 4 h; Stage #2: With water in dichloromethane

T=0°C; Hide Experimental Procedure

Radomkit, Suttipol; Sarnpitak, Pakornwit; Tummatorn, Jumreang; Batsomboon, Paratchata; Ruchirawat, Somsak; Ploypradith, Poonsakdi

Tetrahedron, 2011 , vol. 67, # 21 p. 3904 - 3914 Title/Abstract Full Text View citing articles Show Details

4) General Procedure C: Preparation of benzyl acetates 9 and 11 General procedure: To a stirred solution of 2,4,5-trimethoxy benzaldehyde (for 9) and 2,5-dimethoxy benzaldehyde (for 11) 1.0 equiv in CH2Cl2 (10 mL/mmol of the starting material) at 0 °C was added AlCl3 (3.0-4.0 equiv), and the reaction mixture was allowed to attain room temperature slowly. After stirring for 4 h at room temperature, the reaction mixture was cooled to 0 °C and very slowly quenched with water and diluted with CH2Cl2. The organic layer was washed with water, brine, dried over Na2SO4 and then concentrated in vacuo to give a white solid which was purified by column chromatography on silica (20percent EtOAc/hexanes) to furnish the demethylated product.

Synthesize Find similar With magnesium chloride in acetonitrile

Reflux;

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Rx-ID: 40564983 Find similar reactions

Xu, You; Yin, Xuguang; Huang, Yi; Du, Pingwu; Zhang, Bin

Chemistry - A European Journal, 2015 , vol. 21, # 12 p. 4571 - 4575 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 35256139 Find similar reactions

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With chloroform; potassium hydroxide in water

T=60°C; Reimer-Tiemann Phenol Formylation; 15 h;

Zhang, Shuai; Wan, Changfeng; Wang, Qiang; Zhang, Baiqun; Gao, Lingfeng; Zha, Zhenggen; Wang, Zhiyong

European Journal of Organic Chemistry, 2013 , # 11 p. 2080 - 2083 Title/Abstract Full Text View citing articles Show Details

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B: 72%

With copper (II) acetate monohydrate in acetonitrile

2 h; Reflux; Hide Experimental Procedure

Xu, Xiangsheng; Huang, Zhenyong; Lu, Yanfeng

Journal of Chemical Research, 2013 , vol. 37, # 9 p. 546 - 549 Title/Abstract Full Text View citing articles Show Details

General procedure: Propargylic alcohol (0.2 mmol) in acetonitrile (2.0 mL) was added Cu(OAc)2·H2O (0.1 mmol) at room temperature. The reaction mixture was heated at reflux, in air. After completion of the reaction as indicated by TLC, the solvent was removed under reduced pressure,and the residue was purified by chromatography on silica gel (100−200 mesh) using petroleum ether/EtOAc (9/1, v/v) as the eluent to give 1,3butadiynes. A

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Rx-ID: 32413601 Find similar reactions

Stage #1: With tetrabutyl ammonium fluoride

T=20°C; 3 h; Inert atmosphere; Stage #2: With water

Yoshioka, Eito; Miyabe, Hideto

Tetrahedron, 2012 , vol. 68, # 1 p. 179 - 189 Title/Abstract Full Text View citing articles Show Details

Hide Experimental Procedure

3.8. General procedure for the reaction of precursors 15-20 in DMF (Table 5)

General procedure: To a solution of TBAF (157 mg, 0.60 mmol) in DMF (1.2 mL) was added a solution of precursors 15-20 (0.20 mmol) in DMF (0.8 mL) under argon atmosphere at room temperature. After being stirred at the same temperature for 3 h, H2O (0.1 mL) was added to the reaction mixture. The reaction mixture was concentrated under reduced pressure. Purification of the residue by flash silica gel column chromatography (AcOEt/hexane=1/20 to 1/3 with 2percent CH2Cl2) afforded the products 21-27. A

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B: 96 %Chromat.

With water in methanol

T=20°C; Irradiation; Quantum yield;

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Kostikov, Alexey P.; Popik, Vladimir V.

Organic Letters, 2008 , vol. 10, # 22 p. 5277 - 5280 Title/Abstract Full Text View citing articles Show Details

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B: 59 %Chromat.

With water in methanol

T=20°C; Irradiation; Quantum yield;

Kostikov, Alexey P.; Popik, Vladimir V.

Organic Letters, 2008 , vol. 10, # 22 p. 5277 - 5280 Title/Abstract Full Text View citing articles Show Details

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B: 100 %Spectr.

With water in methanol

T=20°C; Irradiation; Quantum yield;

Kostikov, Alexey P.; Popik, Vladimir V.

Organic Letters, 2008 , vol. 10, # 22 p. 5277 - 5280 Title/Abstract Full Text View citing articles Show Details

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B: 100 %Spectr.

With water in methanol

T=20°C; Irradiation; Quantum yield;

Kostikov, Alexey P.; Popik, Vladimir V.

Organic Letters, 2008 , vol. 10, # 22 p. 5277 - 5280 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With potassium hydroxide in water; acetone

T=0 - 5°C; 0.5 h; Product distribution / selectivity; Hide Experimental Procedure

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Rx-ID: 23839765 Find similar reactions

Shanks, Thomas Elbert; Maleski, Robert Joseph

Patent: US2003/199714 A1, 2003 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

The black oil from Example 1 (202 g, 82percent assay, 1.1 moles) was dissolved in 900 g of acetone and the solution was cooled to 0-5° C. and treated dropwise with 136 g of 45percent potassium hydroxide solution, holding the temperature below 5° C. The resulting slurry of bright yellow solid was stirred 30 min and filtered. The product cake was washed with 750 g of cold acetone, and dried at room temperature in a nitrogen-purged oven. A total of 210 g of bright yellow product having a weight percent assay of 91percent, was obtained. The overall yield based on 4-methoxyphenol was 67percent With potassium hydroxide in acetone

T=25 - 30°C; 1 h; Product distribution / selectivity; Hide Experimental Procedure

Shanks, Thomas Elbert; Maleski, Robert Joseph

Patent: US2003/199714 A1, 2003 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

The above example was repeated except that 67.8 g of finely ground potassium hydroxide was used in the place of the aqueous solution. It was added at a temperature of 25-30° C. and the resulting solution was stirred for 1 hour at that temperature. The slurry was cooled to 0-5° C. and the product was isolated as in Example 2. The weight percent assay of the product was 98percent and the overall yield based on the starting 4methoxyphenol was 72percent

Synthesize Find similar With sodium hydroxide in water; ethyl acetate

T=5°C; 1 h; Hide Experimental Procedure

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Rx-ID: 23839766 Find similar reactions

Shanks, Thomas Elbert; Maleski, Robert Joseph

Patent: US2003/199714 A1, 2003 ; Location in patent: Page/Page column 4; 5 ; Title/Abstract Full Text Show Details

The black oil from Example 1 (45.9 g, 82percent assay, 0.25 moles moles) was dissolved in 100 g of ethyl acetate and the solution was cooled to 0-5° C. and treated dropwise with 20 g of 50percent sodium hydroxide solution, holding the temperature below 5° C. The resulting slurry of bright yellow solid was stirred 1 hour and filtered. The product cake was washed with 75 g of cold ethyl acetate, and dried at room temperature in a nitrogen-purged oven. A total of 39.1 g of bright yellow product, weight percent assay by HPLC of 72percent (area percent was 98.4) was obtained. The overall yield based on 4-methoxyphenol was 48percent A

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Rx-ID: 8941462 Find similar reactions

B: 32%

in trifluoroacetic acid

24 h;

Sharghi; Nasseri; Niknam

Journal of Organic Chemistry, 2001 , vol. 66, # 22 p. 7287 - 7293 Title/Abstract Full Text View citing articles Show Details

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A: 30% B: 65%

With tetra-n-butylammonium tetrafluoroborate; [Ni(2,2'bipyridine)3(2+)][BF4(1-)]2 in N,Ndimethyl-formamide

electrochem. reaction; magnesium rod anode, nickel foam grid cathode;

Franco, Delphine; Dunach, Elisabet

Tetrahedron Letters, 1999 , vol. 40, # 15 p. 2951 - 2954 Title/Abstract Full Text View citing articles Show Details

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With hydroxide in 1,4dioxane; water

T=37°C; var. temp., ΔH(excit.), ΔS)(excit.); Rate constantThermodynamic data;

Bowden; Huntington; Powell

European Journal of Medicinal Chemistry, 1998 , vol. 32, # 12 p. 987 - 993 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With ethylmagnesium bromide; triethylamine

1.) THF, RT, 20 min, 2.) C6H6, reflux, 2.5 h; Yield given. Multistep reaction;

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Rx-ID: 6331396 Find similar reactions

Wang; You; Meng; Mintz; Bu

Synthetic Communications, 1994 , vol. 24, # 12 p. 1757 - 1760 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 6331395 Find similar reactions

Rubenstein

Journal of the Chemical Society, 1925 , vol. 127, p. 2003 Full Text Show Details

Tiemann; Mueller

Chemische Berichte, 1881 , vol. 14, p. 1986 Full Text Show Details

Malesani et al.

Chimica Therapeutica, 1970 , vol. 5, p. 255,256,258 Full Text Show Details

Dean et al.

Tetrahedron Letters, 1966 , p. 4153,4157 Full Text Show Details

Gassman; Amick

Tetrahedron Letters, 1974 , p. 3463 Full Text View citing articles Show Details

Gassman; Amick

Journal of the American Chemical Society, 1978 , vol. 100, p. 7611,7615 Full Text Show Details

Montedison S.p.A.

Patent: DE2736523 , 1978 ; Chem.Abstr., vol. 88, # 152247 Full Text Show Details

Narasimhan et al.

Synthesis, 1979 , p. 906 Full Text Show Details

Casiraghi et al.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1978 , p. 322 Full Text Show Details

Fuji Photo Film Co.

Patent: DE2331520 , 1974 ; Chem.Abstr., vol. 80, # 122415 Full Text Show Details

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Ethyl Corporation

Patent: US4837327 A1, 1989 ; Title/Abstract Full Text Show Details

A few illustrative examples of preferred aldehydes include ... 3-hydroxy-p-anisaldehyde 3-hydroxybenzaldehyde 4-hydroxybenzaldehyde 2-hydroxy-4-methoxybenzaldehyde 2-hydroxy-5-methoxybenzaldehyde 2-hydroxy-1-naphthaldehyde 5-iodovanillin isophthalaldehyde ...

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Ciba-Geigy Corporation

Patent: US4183553 A1, 1980 ; Title/Abstract Full Text Show Details

The colour formers of the formulae (12) to (17) listed in Table 1 are obtained by carrying out the procedure of Direction 1 and replacing the 3-diethylaminosalicylaldehyde by equimolar amounts of each of the following aldehydes: 5-nitro-salicylaldehyde 5-methoxysalicylaldehyde salicylaldehyde 2-hydroxynaphthaldehyde 3-bromo-5-nitrosalicylaldehyde or 3-nitrosalicylaldehyde.

Synthesize Find similar With trifluoroacetic acid

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Rx-ID: 3608846 Find similar reactions

Carter, Stephen D.; Wallace, Timothy W.

Journal of Chemical Research, Miniprint, 1985 , # 5 p. 1601 - 1633 Title/Abstract Full Text Show Details

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Rx-ID: 18872049 Find similar reactions

Multi-step reaction with 2 steps 1: 12 percent / t-BuOK, CuCl, pyridine / 1,2-dimethoxy-ethane / 3 h / Heating 2: CF3COOH View Scheme

Carter, Stephen D.; Wallace, Timothy W.

Journal of Chemical Research, Miniprint, 1985 , # 5 p. 1601 - 1633 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: 1.) CuCl, 2.) pyridine, 1,3dinitrobenzene / 1.) DME, 2.) reflux, 3h 2: CF3COOH View Scheme

Carter, Stephen D.; Wallace, Timothy W.

Journal of Chemical Research, Miniprint, 1985 , # 5 p. 1601 - 1633 Title/Abstract Full Text Show Details

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Synthesize Find similar Carter, Stephen D.; Wallace, Timothy W.

Rx-ID: 18880694 Find similar reactions

1: 59 percent / I2, H5IO6 / acetic acid; H2O; H2SO4 / 2 h / 80 °C 2: 12 percent / t-BuOK, CuCl, pyridine / 1,2-dimethoxy-ethane / 3 h / Heating 3: CF3COOH View Scheme

Journal of Chemical Research, Miniprint, 1985 , # 5 p. 1601 - 1633 Title/Abstract Full Text Show Details

Multi-step reaction with 3 steps 1: 59 percent / I2, H5IO6 / acetic acid; H2O; H2SO4 / 2 h / 80 °C 2: 1.) CuCl, 2.) pyridine, 1,3dinitrobenzene / 1.) DME, 2.) reflux, 3h 3: CF3COOH View Scheme

Carter, Stephen D.; Wallace, Timothy W.

Journal of Chemical Research, Miniprint, 1985 , # 5 p. 1601 - 1633 Title/Abstract Full Text Show Details

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Rx-ID: 2951439 Find similar reactions

With Me2S(SMe)BF4; water

1.) CH2Cl2, room temp., 2 h; Yield given. Multistep reaction;

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Smith, Robin A. J.; Bin Manas, Abdul Rahman

Synthesis, 1984 , # 2 p. 166 - 168 Title/Abstract Full Text Show Details

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Rx-ID: 3343407 Find similar reactions

With N,N,N',N,tetramethylethylenediamine; sec.butyllithium

1.) THF, -78 deg C, 1 h, 2.) to room temp., 8 to 12 h; Yield given. Multistep reaction. Yields of byproduct given;

Sibi, Mukund P.; Snieckus, Victor

Journal of Organic Chemistry, 1983 , vol. 48, # 11 p. 1935 - 1937 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2951808 Find similar reactions

Reimer-Tiemann reaction;

Verhe; De Kimpe; De Buyck; et al.

Bulletin des Societes Chimiques Belges, 1980 , vol. 89, # 6 p. 459 - 485 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 40 percent / BF3*Et2O / CH2Cl2 / 14 h / Ambient temperature 2: 47 percent / H2O, HgO, BF3*Et2O / tetrahydrofuran / 1 h / Ambient temperature View Scheme

Jo, Shigeo; Tanimoto, Shigeo; Sugimoto, Toyonari; Okano, Masaya

Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 7 p. 2120 - 2123 Title/Abstract Full Text Show Details

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With boron trifluoride diethyl etherate; water; mercury(II) oxide in tetrahydrofuran

1 h; Ambient temperature;

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Rx-ID: 3255288 Find similar reactions

Jo, Shigeo; Tanimoto, Shigeo; Sugimoto, Toyonari; Okano, Masaya

Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 7 p. 2120 - 2123 Title/Abstract Full Text Show Details

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Rx-ID: 1626544 Find similar reactions

Jackman,L.M.; Trewella,J.C.; Haddon,R.C.

Journal of the American Chemical Society, 1980 , vol. 102, p. 2519

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Montedison S.p.A.

Patent: US4151201 A1, 1979 ; Title/Abstract Full Text Show Details

11:2-hydroxy-5-methoxybenzaldehyde

EXAMPLE 11 2-hydroxy-5-methoxybenzaldehyde By operating according to Example 1 and starting from 12.4 g (0.1 mole) of 4-methoxyphenol, 6.8 g of a product having a boiling point at 247°-248° C., distilled between 115° and 120° C. at 16 mm/Hg, were obtained. The centesimal, infrared and nuclear magnetic resonance analyses agreed with the structure: C8 H8 O3.

Synthesize Find similar (i) SOCl2, Py, PE, (ii) H2, quinoline, sulfur, Pd-BaSO4, xylene; Multistep reaction;

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Rx-ID: 1089954 Find similar reactions

Amakasu,T.; Sato,K.

Bulletin of the Chemical Society of Japan, 1967 , vol. 40, p. 1428 - 1432 Full Text View citing articles Show Details

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Rx-ID: 301025 Find similar reactions

in ein zuvor auf 165grad erhitztes Gemisch von Glycerin und Borsaeure bei 150grad und Behandeln des Reaktionsgemisches mit wss.H2SO4 bei 115grad;

Diehl et al.

Iowa State College Journal of Science, 1947 , vol. 22, p. 91,108 Full Text Show Details

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Rx-ID: 753285 Find similar reactions

With sodium hydroxide

Hodgson; Beard

Journal of the Chemical Society, 1927 , p. 2340 Full Text Show Details

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Multi-step reaction with 2 steps 1: potassium persulfate; NaOHsolution; alkali / 30 - 35 °C / und Erhitzen des Reaktionsprodukts mit konz.Salzsaeure auf 70grad 2: aqueous NaOH-solution View Scheme

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Journal of the Chemical Society, 1927 , p. 2340 Full Text Show Details

Rx-ID: 22064043 Find similar reactions

Synthesize Find similar Rx-ID: 7444862 Find similar reactions

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Tiemann; Mueller

Chemische Berichte, 1881 , vol. 14, p. 1986 Full Text Show Details

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