Benzene-1,3,5-triol (Phloroglucinol) by Asch

Reaxys

PubChem

eMolecules

Reactions (223)

Yield

Substances (7)

Citations (202)

Conditions

References

Synthesize Find similar With hydrogenchloride; water

T=100°C; 18 h; Product distribution / selectivity; Hide Experimental Procedure

Synthesize Find similar

Rx-ID: 23495852 Find similar reactions

PHV ANALYITIC

Patent: US2005/165256 A1, 2005 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

EXAMPLE 3; Hydrolysis of 1,3,5-triaminobenzene to phloroglucinol and its extraction with ethyl ether; 2.2 g (18 mmol) of 1,3,5-triaminobenzene in 150 ml of a 2 N aqueous solution of hydrochloric acid are heated at 100° C. for 18 h. After cooling to ambient temperature, the solution is filtered. The aqueous phase is subsequently extracted with 3.x.40 ml of ethyl ether. The ethereal phases are dried over sodium sulfate, filtered and then evaporated. The phloroglucinol obtained is subsequently recrystallized from 17 ml of water containing 15 mg of active carbon, giving 1.5 g of pure phloroglucinol. With hydrogenchloride; water

T=120°C; 15 h; Product distribution / selectivity; Hide Experimental Procedure

PHV ANALYITIC

Patent: US2005/165256 A1, 2005 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

EXAMPLE 4; Hydrolysis of 1,3,5-triaminobenzene to phloroglucinol and its purification with ethyl ether; 5 g of 1,3,5-triaminobenzene in 300 ml of a 0.5 N aqueous solution of hydrochloric acid are heated at 120° C. for 15 hours. After cooling, the solution is concentrated until the phloroglucinol precipitates. The filtered precipitate is recrystallized from 40 ml of water with active carbon. The product obtained is subsequently taken up in a minimum of ethyl ether and heated for 15 minutes with active carbon.

Evaporation gives 2.9 g of pure product. With water

Mechanism;

Belskaya, Olga B.; Talsi, Valentin P.; Mironenko, Roman M.; Rodionov, Vladimir A.; Sysolyatin, Sergey V.; Likholobov, Vladimir A.

Journal of Molecular Catalysis A: Chemical, 2016 , vol. 420, p. 190 - 199 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 80%

With aluminum (III) chloride in chlorobenzene

8 h; Reflux; Solvent; Hide Experimental Procedure

Synthesize Find similar

Rx-ID: 44537028 Find similar reactions

Shouguang Fukang Pharmaceutical Co.,Ltd; Shandong Fukang biotechnology Productivity Promotion Center; Shouguang Yongkang Chemical Industry Co., Ltd; Zhu, Suyuan; Dong, Liangjun; Plauks, Peter; Lin, WenHan; Song, Weiguo; Yang, Lei

Patent: CN103755529 B, 2016 ; Location in patent: Paragraph 0038; 0040 ; Title/Abstract Full Text Show Details

3:synthesis of phloroglucinol

With a reflux condenser, dropping funnel, Stirring in a 1000 mL three-necked flask 50 g of 1,3,5-trimethoxybenzene, 240 g of aluminum trichloride, chlorobenzene 300 mL, Stirring, Heated to reflux for 8 hours, Cool to room temperature. Dropping 2mol/L HCl dilute solution 500mL layer, The aqueous layer was extracted twice with chlorobenzene (200 mL each) The organic layers were combined, The solvent was recovered under reduced pressure, The residual solid was recrystallized from water, activated carbon decolorization, dry, a white phloroglucinol product 30 g (content 98.5percent), Yield 80percent.

Synthesize Find similar With water-d2

Inert atmosphereReflux;

Synthesize Find similar

Rx-ID: 40280447 Find similar reactions

Giese, Michael; Krappitz, Tim; Dong, Ronald Y.; Michal, Carl A.; Hamad, Wadood Y.; Patrick, Brian O.; MacLachlan, Mark J.

Journal of Materials Chemistry C, 2015 , vol. 3, # 7 p. 1537 - 1545 Title/Abstract Full Text View citing articles Show Details

Synthesize

Synthesize Find similar

Rx-ID: 33164020 Find similar reactions

With monoacetylphloroglucinol acetyltransferase

T=25°C; pH=7; aq. phosphate bufferEnzymatic reaction; Kinetics;

Find similar

Hayashi, Asuka; Saitou, Hiroki; Mori, Tomomi; Matano, Ikue; Sugisaki, Hiroyuki; Maruyama, Kiyofumi

Bioscience, Biotechnology and Biochemistry, 2012 , vol. 76, # 3 p. 559 - 566 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 98%

With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate

T=20°C; 0.116667 h; Green chemistry; Hide Experimental Procedure

Synthesize Find similar

Rx-ID: 34452739 Find similar reactions

Shirini, Farhad; Khaligh, Nader Ghaffari; Akbari-Dadamahaleh, Somayeh

Journal of Molecular Catalysis A: Chemical, 2012 , vol. 365, p. 15 - 23 Title/Abstract Full Text View citing articles Show Details

General procedure for the deprotection of trimethylsilyl ethers

General procedure: A mixture of the substrate (1 mmol), ionic liquid [Dsim]HSO4 (6.5 mg, ∼0.02 mmol) in methanol (2 mL) was stirred at room temperature. After completion of the reaction (monitored by TLC), solvent was evaporated, water (1 mL) was added to the mixture, and stirred vigorously. Decantation of the mixture gave almost pure product(s). The products were characterized by comparison of their IR and NMR data. The ionic liquid was dried at 65 ◦C under vacuum to remove moisture, and then reused. 87%

With methanol

T=20°C; 0.333333 h; Hide Experimental Procedure

Shirini, Farhad; Atghia, Seyyed Vahid; Jirdehi, Mojtaba Ghazi

Catalysis Communications, 2012 , vol. 18, p. 5 - 10 Title/Abstract Full Text View citing articles Show Details

2.5. General procedure for deprotection of trimethylsilyl ethers

General procedure: A mixture of the substrate (1 mmol) and TiO2–HClO4 (5 mg) in methanol (1 mL) was stirred at room temperature. After completion of the reaction (indicated by TLC), the catalyst was filtered off and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to afford pure alcohols and phenols (Table 2). A

Synthesize Find similar

Synthesize Find similar Rx-ID: 28823822 Find similar reactions

Alkaline aq. solution;

Novruzov; Abdullaeva; Shamsizade; Mustafaev

Chemistry of Natural Compounds, 2009 , vol. 45, # 2 p. 249 - 250 Title/Abstract Full Text View citing articles Show Details

Alkaline conditions;

Alaniya; Kavtaradze; Skhirtladze; Sutiashvili

Chemistry of Natural Compounds, 2011 , vol. 47, # 3 p. 377 - 381 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 96%

Stage #1: With potassium hydroxide in water

T=130°C; 2 h; Stage #2: With hydrogenchloride in water

T=20°C;

Synthesize Find similar

Rx-ID: 31756706 Find similar reactions

Zhang, Qingzhi; Botting, Nigel P.; Kay, Colin

Chemical Communications, 2011 , vol. 47, # 38 p. 10596 - 10598 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 429111 Find similar reactions

With potassium carbonate

beim Schmelzen;

Hlasiwetz

Justus Liebigs Annalen der Chemie, 1859 , vol. 112, p. 98 Full Text View citing articles Show Details

Hlasiwetz; Pfaundler

Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1864 , p. 561 Full Text View citing articles Show Details

With potassium hydroxide

Herzig

Monatshefte fuer Chemie, 1885 , vol. 6, p. 872 Full Text View citing articles Show Details

With potassium hydroxide

Herzig

Monatshefte fuer Chemie, 1885 , vol. 6, p. 872 Full Text View citing articles Show Details

With potassium hydroxide

Hydrolysis;

Abdullazhanova; Mavlyanov; Abdullaev

Chemistry of Natural Compounds, 2000 , vol. 36, # 1 p. 97 - 98 Title/Abstract Full Text View citing articles Show Details

With potassium hydroxide

Heating;

Guzhva

Chemistry of Natural Compounds, 2010 , vol. 46, # 2 p. 303 - 304 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 8622519 Find similar reactions

With potassium hydroxide

Hydrolysis;

Abdullazhanova; Mavlyanov; Abdullaev

Chemistry of Natural Compounds, 2000 , vol. 36, # 1 p. 97 - 98 Title/Abstract Full Text View citing articles Show Details

With potassium hydroxide

Heating;

Guzhva

Chemistry of Natural Compounds, 2010 , vol. 46, # 2 p. 303 - 304 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With Oxonereg; in water; acetone

T=20°C; 0.5 h;

Synthesize Find similar

Rx-ID: 29444108 Find similar reactions

Marshall, Laura J.; Cable, Karl M.; Botting, Nigel P.

Tetrahedron Letters, 2010 , vol. 51, # 20 p. 2690 - 2692 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 29714071 Find similar reactions

With water; potassium hydroxide

T=150 - 230°C; 0.0833333 h; Inert atmosphere;

Nishanbaev; Khidyrova; Vdovin; Abdullaev; Shakhidoyatov; Aripov

Chemistry of Natural Compounds, 2010 , vol. 46, # 3 p. 357 - 362

Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 29714075 Find similar reactions

With water; potassium hydroxide

T=150 - 230°C; 0.0833333 h; Inert atmosphere;

Nishanbaev; Khidyrova; Vdovin; Abdullaev; Shakhidoyatov; Aripov

Chemistry of Natural Compounds, 2010 , vol. 46, # 3 p. 357 - 362 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 29716280 Find similar reactions

With water; potassium hydroxide

HeatingInert atmosphere;

Alimova; Nishanbaev; Vdovin; Abdullaev; Aripova

Chemistry of Natural Compounds, 2010 , vol. 46, # 3 p. 352 - 356 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 29716286 Find similar reactions

With water; potassium hydroxide

Alimova; Nishanbaev; Vdovin; Abdullaev; Aripova

HeatingInert atmosphere;

Chemistry of Natural Compounds, 2010 , vol. 46, # 3 p. 352 - 356 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

B: 89%

Hide Experimental Procedure

Rx-ID: 29936325 Find similar reactions

Vercauteren, Joseph

Patent: US2010/310615 A1, 2010 ; Title/Abstract Full Text Show Details

1:O-alkylation of Phloroglucinol

EXAMPLE 1 O-alkylation of Phloroglucinol 1.560 g of phloroglucinol (12.3 mmol) are dissolved in 20 ml of anhydrous acetone in a double-necked flask with a top-mounted condenser. With stirring under an argon atmosphere, in the presence of 1.685 g (12.3 mmol, 2 chemical eq) of potassium carbonate (K2CO3), 766 microliters of methyl iodide are added (=1.746 g; d=2.28 g/ml at 25° C.), i.e., 12.3 mmol=1 molar equivalent relative to the resveratrol. The reaction is heated at reflux for 3 hours. The reaction mixture is filtered on a No. 4 frit to remove the K2CO3, and the acetone is evaporated under vacuum. The residue is taken up in 15 ml of ethyl acetate. The organic phase is washed with 2 times 15 ml of distilled water, dried over sodium sulfate, filtered and evaporated to dryness to leave a residue of 1357 mg, which is identified as 5-methoxyresorcinol (crude yield=89percent; mw=124) on the basis of its spectral constants: 1H NMR, acetone-d6, 500 MHz, δ ppm: 5.95 (1H, d); 5.90 (2H, d); 3.65 (3H, s, CH3). 13C

NMR, acetone-d6, 125 MHz, δ ppm: 167.2 (s); 164.22 (2 s); 100.61 (d); 98.26 (2 d); 59.6 (quad.).

Synthesize Find similar

81%

With boron tribromide in dichloromethane

T=-78 - 20°C; 19 h;

Synthesize Find similar

Rx-ID: 31267826 Find similar reactions

Marshall, Laura J.; Cable, Karl M.; Botting, Nigel P.

Journal of Labelled Compounds and Radiopharmaceuticals, 2010 , vol. 53, # 10 p. 601 - 604 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Multi-step reaction with 3 steps 1: [Ir2(OMe)2(1,5-cyclooctadiene)2]; caesium carbonate / 2,4-dimethylbutane / 18 h / 100 °C / Inert atmosphere 2: Oxonetrade; / water; acetone / 20 °C 3: boron tribromide / dichloromethane / 19 h / -78 20 °C View Scheme

Synthesize Find similar

Rx-ID: 31267828 Find similar reactions

Marshall, Laura J.; Cable, Karl M.; Botting, Nigel P.

Journal of Labelled Compounds and Radiopharmaceuticals, 2010 , vol. 53, # 10 p. 601 - 604 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Multi-step reaction with 2 steps 1: Oxonetrade; / water; acetone / 20 °C 2: boron tribromide / dichloromethane / 19 h / -78 20 °C View Scheme

Synthesize Find similar

Rx-ID: 31267831 Find similar reactions

Marshall, Laura J.; Cable, Karl M.; Botting, Nigel P.

Journal of Labelled Compounds and Radiopharmaceuticals, 2010 , vol. 53, # 10 p. 601 - 604 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 28185227 Find similar reactions

Alkaline conditions;

Alaniya; Kavtaradze; Skhirtladze

Chemistry of Natural Compounds, 2008 , vol. 44, # 5 p. 673 - 674 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 11019543 Find similar reactions

With ammonium hydroxide; air in ethanol; water

pH=10.0; 3.5 h;

Zenkevich, Igor G.; Eshchenko, Anna Yu.; Makarova, Svetlana V.; Vitenberg, Alexander G.; Dobryakov, Yuri G.; Utsal, Viktor A.

Molecules, 2007 , vol. 12, # 3 p. 654 - 672 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 275801 Find similar reactions

With hydrogenchloride; tin

Kochen der neutralisierten Reaktionsfluessigkeit mit Natronlauge;

Organic Syntheses 9 <New York 1929>, S. 74 Full Text Show Details

Multi-step reaction with 2 steps 1: Fe; HCl 2: H2SO4 / 108 °C View Scheme

Achkar, Jihane; Xian, Mo; Zhao, Huimin; Frost

Journal of the American Chemical Society, 2005 , vol. 127, # 15 p. 5332 - 5333 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

56%

With hydrogenchloride in water

36 h;

Synthesize Find similar

Rx-ID: 9870235 Find similar reactions

Hansen, Chad A.; Frost

Journal of the American Chemical Society, 2002 , vol. 124, # 21 p. 5926 - 5927

Title/Abstract Full Text View citing articles Show Details

With hydrogenchloride

Achkar, Jihane; Xian, Mo; Zhao, Huimin; Frost

Journal of the American Chemical Society, 2005 , vol. 127, # 15 p. 5332 - 5333 Title/Abstract Full Text View citing articles Show Details

Hide Experimental Procedure

Andeno B.V.

Patent: US3959388 A1, 1976 ; Title/Abstract Full Text Show Details

3:EXAMPLE 3

A residue containing 34 g phloroglucinol monomethyl ether and 12 g phloroglucinol was obtained.

Synthesize Find similar

With sulfuric acid

T=108°C;

Synthesize Find similar

Rx-ID: 9880258 Find similar reactions

Achkar, Jihane; Xian, Mo; Zhao, Huimin; Frost

Journal of the American Chemical Society, 2005 , vol. 127, # 15 p. 5332 - 5333 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 10033640 Find similar reactions

Stage #1: With 2-hydroxy-1,3isoindolinedione; 2,2'-azobisisobutyronitrile; oxygen in acetonitrile

T=75°C; P=760 Torr; 2 h; Stage #2: With sulfuric acid in acetonitrile

T=20°C; 2 h; Title compound not separated from byproducts;

Aoki, Yasuhiro; Hirai, Naruhisa; Sakaguchi, Satoshi; Ishii, Yasutaka

Tetrahedron, 2005 , vol. 61, # 46 p. 10995 - 10999 Title/Abstract Full Text View citing articles Show Details

Stage #1: With 2-hydroxy-1,3isoindolinedione; 2,2'-azobisisobutyronitrile; oxygen in acetonitrile

T=75°C; P=22800 Torr; 24 h; Stage #2: With sulfuric acid in acetonitrile

T=20°C; 2 h; Title compound not separated from byproducts;

Aoki, Yasuhiro; Hirai, Naruhisa; Sakaguchi, Satoshi; Ishii, Yasutaka

Tetrahedron, 2005 , vol. 61, # 46 p. 10995 - 10999 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Multi-step reaction with 3 steps 1: NaCr2O7; H2SO4

2: Fe; HCl 3: H2SO4 / 108 °C View Scheme

Synthesize Find similar

Rx-ID: 13087963 Find similar reactions

Achkar, Jihane; Xian, Mo; Zhao, Huimin; Frost

Journal of the American Chemical Society, 2005 , vol. 127, # 15 p. 5332 - 5333 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

40%

Stage #1: With ammonia; copper(l) iodide in water

T=180°C; P=30003 Torr; 24 h; Stage #2: With hydrogenchloride; water

T=0 - 120°C; 20 h; Product distribution / selectivity; Hide Experimental Procedure

Synthesize Find similar

Rx-ID: 23486318 Find similar reactions

PHV ANALYITIC

Patent: US2005/165256 A1, 2005 ; Location in patent: Page/Page column 3-4 ; Title/Abstract Full Text Show Details

EXAMPLE 1; Preparation of 1,3,5-triaminobenzene from 1,3,5-trichlorobenzene and its hydrolysis to phloroglucinol; A pressurized vessel is charged with 5 g (27.5 mmol) of 1,3,5-trichlorobenzene and 70 ml of 28percent aqueous ammonia and 800 mg of copper iodide are added. The mixture is heated at 180° C. and at a pressure of 40 bar for 24 h. After the mixture has cooled, 40 g of crushed ice and 79 ml of concentrated hydrochloric acid are added and then the mixture is heated at 120° C. for 20 h. The contents of the flask are filtered. The filtrate is subsequently extracted with 3*40 ml of ethyl ether.

Synthesize

Find similar

60%

Stage #1: With ammonia; copper(l) iodide in water

T=180°C; P=30003 Torr; 24 h; Stage #2: With hydrogenchloride; water

T=0 - 120°C; pH=1; 20 h; Product distribution / selectivity; Hide Experimental Procedure

Find similar

Rx-ID: 23491486 Find similar reactions

PHV ANALYITIC

Patent: US2005/165256 A1, 2005 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

EXAMPLE 2; Preparation of 1,3,5-triaminobenzene from 3,5-dichloroaniline and its hydrolysis to phloroglucinol; A pressurized vessel is charged with 3 g (18.5 mmol) of 3,5-dichloroaniline and 50 ml of 28percent aqueous ammonia and 300 mg of copper iodide are added. The mixture is heated at 180° C. and at a pressure of 40 bar for 24 h. After the mixture has been cooled, 30 g of crushed ice and a concentrated, 37percent solution of hydrochloric acid are added to a pH of 1, and then the mixture is heated at 120° C. for 20 h. The contents of the flask are filtered. The filtrate is subsequently extracted with 3*40 ml of ethyl ether, dried and then evaporated. This gives a phloroglucinol yield of the order of 60percent.

Stage #1: With ammonia; copper(l) chloride in water

T=190°C; P=27752.8 Torr; 24 h; Stage #2: With sulfuric acid; water

T=110°C; 20 h; Product distribution / selectivity; Hide Experimental Procedure

PHV ANALYITIC

Patent: US2005/165256 A1, 2005 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

EXAMPLE 6; Preparation of 1,3,5-triaminobenzene from 3,5-dichloroaniline; hydrolysis with sulfuric acid of the 1,3,5-triaminobenzene to phloroglucinol, and purification; A pressurized vessel is charged with 30 g (18.6 mmol) of 3,5-dichloroaniline and 1.5 g of copper chloride in 160 ml of 28percent aqueous ammonia. The mixture is heated at 190° C. and under a pressure of 37 bars for 24 hours. The contents of the vessel are poured into 200 ml of water and then the excess ammonia is removed. Then 37 g of 98percent sulfuric acid are added and the mixture is heated at 110° C. for 20 hours. Following filtration, the solution is concentrated to a third and then cooled in an ice bath until the phloroglucinol precipitates. The precipitate obtained is subsequently recrystallized from 350 ml of a water-ethanol (93 V-7 V) mixture.

Stage #1: With ammonia; copper(l) iodide in water

T=190°C; P=30003 Torr; 24 h; Stage #2: With hydrogenchloride; water

T=110°C; 20 h; Product distribution / selectivity; Hide Experimental Procedure

PHV ANALYITIC

Patent: US2005/165256 A1, 2005 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

EXAMPLE 5; Preparation of 1,3,5-triaminobenzene from 3,5-dichloroaniline, hydrolysis with hydrochloric acid of the 1,3,5-triaminobenzene to phloroglucinol; A pressurized vessel is charged with 30 g (18.6 mmol) of 3.5-dichloroaniline and 1.8 g of copper iodide in 160 ml of 28percent aqueous ammonia. The mixture is heated at 190° C. and under a pressure of 40 bars for 24 h. The contents of the vessel are poured into 200 ml of water and then the excess ammonia is removed. Then 56 g of 10 N hydrochloric acid are added and the mixture is heated at 110° C. for 20 h. Following filtration, the solution is cooled in an ice bath until the phloroglucinol precipitates. The precipitate obtained is subsequently recrystallized from 400 ml of a water-methanol (95 V-5 V) mixture.

Synthesize Find similar

87%

With amberlyst-15 in methanol

T=20°C; 4 h;

Synthesize Find similar

Rx-ID: 9391817 Find similar reactions

Das, Biswanath; Banerjee, Joydeep; Ramu; Pal, Rammohan; Ravindranath; Ramesh

Tetrahedron Letters, 2003 , vol. 44, # 29 p. 5465 - 5468 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

95%

With tin(IV) chloride in 1,2-dichloro-ethane

Heating;

Synthesize Find similar

Rx-ID: 9188967 Find similar reactions

Hadjeri, Mohamed; Mariotte, Anne-Marie; Boumendjel, Ahcene

Journal of Chemical Research - Part S, 2002 , # 9 p. 463 - 464 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Multi-step reaction with 2 steps 1: Acid hydrolysis 2: KOH View Scheme

Synthesize Find similar

Rx-ID: 15755830 Find similar reactions

Abdullazhanova; Mavlyanov; Abdullaev

Chemistry of Natural Compounds, 2000 , vol. 36, # 1 p. 97 - 98 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 4581754 Find similar reactions

With sodium hydroxide; hydroxylamine; silica gel

1.) aqueous EtOH, reflux, 2.) heat.; Yield given. Multistep reaction. Yields of byproduct given;

Munakata, Tatsuo; Ooi, Takashi; Kusumi, Takenori

Tetrahedron Letters, 1997 , vol. 38, # 2 p. 249 - 250 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Rx-ID: 4582055 Find similar reactions

With sodium hydroxide; hydroxylamine; silica gel

1.) aqueous EtOH, reflux, 2.) heat; Multistep reaction;

Synthesize Find similar

Munakata, Tatsuo; Ooi, Takashi; Kusumi, Takenori

Tetrahedron Letters, 1997 , vol. 38, # 2 p. 249 - 250 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3385054 Find similar reactions

With acetic acid in ethanol

T=95°C; 0.75 h;

Foo; Newman; Waghorn; Mcnabb; Ulyatt

Phytochemistry, 1996 , vol. 41, # 2 p. 617 - 624 Title/Abstract Full Text View citing articles Show Details

With acetic acid in ethanol

T=95°C; 1 h; Product distribution;

Foo, Lai Yeap; Karchesy, Joseph J.

Phytochemistry (Elsevier), 1989 , vol. 28, # 11 p. 3185 - 3190 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Rx-ID: 3385055 Find similar reactions

Synthesize Find similar

With acetic acid in ethanol

T=95°C; 0.75 h;

Foo; Newman; Waghorn; Mcnabb; Ulyatt

Phytochemistry, 1996 , vol. 41, # 2 p. 617 - 624 Title/Abstract Full Text View citing articles Show Details

With acetic acid in ethanol

T=95°C; 1 h; Product distribution;

Foo, Lai Yeap; Karchesy, Joseph J.

Phytochemistry (Elsevier), 1989 , vol. 28, # 11 p. 3185 - 3190 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

90%

Hide Experimental Procedure

Rx-ID: 6502239 Find similar reactions

Sumitomo Chemical Company, Limited

Patent: US4463199 A1, 1984 ; Title/Abstract Full Text Show Details

R.1:REFERENCE EXAMPLE 1

Thereafter, phloroglucin obtained from the MIBK layer after extraction and the filtrate after recrystallization was recycled to the concentrated solution to carry out purification similarly. Thus, about 52 g of anhydrous phloroglucin was obtained as white crystal on and after the second operation. Purity, not less than 98percent; m.p., 217°-219° C.; purification yield, 90percent; and overall yield of from decomposition to purification, about 83percent.

88%

Hide Experimental Procedure

Sumitomo Chemical Company, Limited

Patent: US4463197 A1, 1984 ; Title/Abstract Full Text Show Details

3:EXAMPLE 3

EXAMPLE 3 Purification of the crude phloroglucin was carried out in completely the same condition and method as in Example 2 except that ethyl acetate was used as extraction solvent in place of methyl isobutyl ketone. The phloroglucin obtained had a purity of 98.0percent or more (anhydrous product) and a melting point of 217°-219° C. The purification yield was 88percent.

82%

Hide Experimental Procedure

Akzona Incorporated

Patent: US4071555 A1, 1978 ; Title/Abstract Full Text Show Details

7:EXAMPLE 7

EXAMPLE 7 Analogous to Example 6, 20 g (80.3 mmole) of benzene-1,3,5-trisacetoxime in 275 ml trifluoroacetic acid were heated to 140° C for 50 minutes (closed system), whereupon the solvent was remoed in a vaccum. The remaining brown crystal mass was then suspended in 350 ml of 0.75 N sulfuric acid with vigorous agitation and heated to 160°-170° C for 12 hours (corresponding to an inherent partial pressure of 10 to 14 atmospheres gauge pressure). A dark, clear solution was formed thereby, which was neutralized with soda and extracted with ether. In this manner it was possible to obtain 8.38 g (66 mmole), corresponding to 82percent of the theoretical yield of phloroglucinol, based on the charged benzene- 1,3,5-trisacetoxime, from the ether extract. Hide Details

Szell,T. et al.

Tetrahedron, 1969 , vol. 25, p. 707 - 714 Full Text View citing articles Show Details

Royer,R. et al.

Bulletin de la Societe Chimique de France, 1973 , p. 611 - 615 Full Text View citing articles Show Details

Ghosal; Dutta

Phytochemistry (Elsevier), 1971 , vol. 10, p. 195,197 Full Text Show Details

Floss; Rettig

Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, 1964 , vol. 19, p. 1103

Full Text Show Details

Chauhan; Saraswat

Journal of the Indian Chemical Society, 1978 , vol. 55, # 10 p. 1049 - 1051 Title/Abstract Full Text View citing articles Show Details

Dubey; Misra

Journal of the Indian Chemical Society, 1976 , vol. 53, p. 378,380 Full Text Show Details

Hunt; Rigby

Journal of the Chemical Society [Section] C: Organic, 1970 , p. 2459,2461 Full Text Show Details

Morton International, Inc.

Patent: US3230266 , 1961 ; Chem.Abstr., 1966 , vol. 64, # 9640b Full Text Show Details

Givaudan and Cie.

Patent: FR2344518DE2705874 , 19771977 ; Chem.Abstr., vol. 87, # 167718 Full Text Show Details

Newhall; Ting

Journal of Agricultural and Food Chemistry, 1967 , vol. 15, p. 776 Full Text View citing articles Show Details

Kampouris

Journal of the Chemical Society, 1965 , p. 2651 Full Text Show Details

Ceshire et al.

Tetrahedron, 1968 , vol. 24, p. 5155,5156,5157,5159,5163 Full Text View citing articles Show Details

Mc Killop et al.

Synthetic Communications, 1974 , vol. 4, p. 35 Full Text Show Details

Chirikdjian et al.

Monatshefte fuer Chemie, 1969 , vol. 100, p. 1105 Full Text View citing articles Show Details

Hide Experimental Procedure

Ishihara Sangyo Kaisha Ltd.

Patent: US4380670 A1, 1983 ; Title/Abstract Full Text Show Details

3:EXAMPLE 3

After the reaction, nitrogen gas was fed to discharge ammonia gas and hydrochloric acid was added to neutralize the reaction mixture and 6 ml. of hydrochloric acid was further added and water was added to give a total volume of 50 ml. The mixture was refluxed in nitrogen gas flow to hydrolyze the product for 20 hours. The reaction mixture was cooled and the reaction product was extracted with ether, and dried and the solvent was distilled off to obtain 1.5 g. of phloroglucine.

Hide Experimental Procedure

The United States of America as represented by the Secretary of the Navy

Patent: US4434304 A1, 1984 ; Title/Abstract Full Text Show Details

1:EXAMPLE 1

EXAMPLE 1 A solution of 38 ml of 71percent HNO3 (0.608 mole) in 62 ml of 97percent H2 SO4 was added to a mechanically stirred solution of 25.22 g (0.2 mole) of phloroglucinol (obtained from Matheson, Coleman and Bell, anhydrous, m.p. 217°-219° C.) in 500 ml of 97percent H2 SO4 over a one hour period with ice-bath cooling. During addition the temperature of the reaction mixture is maintained at 5°-8° by adjusting the addition rate to maintain a slightly exothermic reaction. After addition is complete, stirring is continued for 9 minutes. The mixture, containing a precipitate, is then poured over 1800 g of ice.

Hide Experimental Procedure

Ishihara Sangyo Kaisha Ltd.

Patent: US4380670 A1, 1983 ; Title/Abstract Full Text Show Details

6:EXAMPLE 6

The reaction mixture was obtained by the same process and ammonia was discharged and hydrochloric acid was added to acidify the reaction mixture. The mixture was refluxed in nitrogen gas flow for 20 hours to hydrolyze the product. After the reaction, the reaction product was purified and recrystallized to obtain 17 g. of phloroglucine.

Hide Experimental Procedure

Sumitomo Chemical Company, Limited

Patent: US4463199 A1, 1984 ; Title/Abstract Full Text Show Details

R.1:REFERENCE EXAMPLE 1

After liquid/liquid separation, 130 g of fresh MIBK was added to the aqueous layer to extract impurities with the MIBK layer, and the aqueous layer was acidified with sulfuric acid and cooled to 15° C. to deposit crystals. The deposited pale yellow crystal of phloroglucin was filtered off. Activated carbon was added to the resulting phloroglucin crystal which was then recrystallized from water, filtered off and dried to obtain about 47 g of anhydrous phloroglucin as white crystal.

Hide Experimental Procedure

The Procter and Gamble Company

Patent: US3957424 A1, 1976 ; Title/Abstract Full Text Show Details

Specific examples of formula (C) compounds are: ... 4-(2-propenoxy)phenol 4-(3-chloro-2-propenoxy)phenol 2-chloro-4-hydroxyphenol 2-amino-4-hydroxyphenol 1,3,5-trihydroxybenzene 2,4-dihydroxybenzaldehyde 3,4-dihydroxybenzaldehyde 3,4-dihydroxybenzoic acid ...

Hide Experimental Procedure

Akzona Incorporated

Patent: US4057588 A1, 1977 ; Title/Abstract Full Text Show Details

3:Preparation of Phloroglucinol

EXAMPLE 3 Preparation of Phloroglucinol 10.1 (40 mmole) 1,3,5-triuredio-benzene was reacted with (11.3 g) 0.31 mole HCl = 31.5 g 36percent hydrochloric acid (corresponding at the end of the reaction to an HCl excess of 2.5 g = 0.5percent HCl solution) in a 1-liter autoclave lined with Teflon for 16 hours at 180° C and a characteristic partial pressure of 20 atm. under vigorous stirring. After completed reaction, the system was cooled, evaporated and the light-brown, clear solution was dried by condensation. 19.1 g of an ocher to light-brown, readily pulverized solid was left behind. (The theoretical amount for 100percent conversion to phloroglucinol and ammonium chloride is calculated at 19.35 l g). 4.83 g of a mixture of phloroglucinol and phloroglucidol was isolated from the product mix by extraction with ethyl acetate, yielding after chromatographic separation 4.23 g (32

Hide Experimental Procedure

Akzona Incorporated

Patent: US4071555 A1, 1978 ; Title/Abstract Full Text Show Details

5:EXAMPLE 6

Rearrangement of Benzene-1,3,5-trisacetoxime and Hydrolysis of the Rearrangement Product to Phloroglucinol without Intermediate Isolation EXAMPLE 6 19.1 g (76.7 mmole) of benzene-1,3,5-trisacetoxime were suspended in 250 ml trifluoroacetic acid in a 500 ml glass autoclave equipped with a Teflon.(R). agitator and thermometer connection and heated to 125° C within 15 minutes with vigorous agitation. This resulted in a clear solution, which, in order to complete the reaction, was left at this temperature for another 40 minutes. Subsequently, the solvent (trifluoroacetic acid) was distilled off, the light brown residue subsequently mixed with 300 ml of a 1N-aqueous hydrochloric acid and decomposed for 20 hours with vigorous agitation at 175° to 180° C. Thereby, an inherent partial pressure of about 15 atmospheres gauge pressure was produced. The dark reaction solution was subsequently concentrated in a vacuum at 50° C and extracted with acetic ester, 8.3 g (67. mmole), corresponding to 87.5percent of theoretical, of phloroglucinol were isolated from the acetic ester extract.

Hide Experimental Procedure

ENICHEM S.p.A.

Patent: EP372623 A3, 1992 ; Title/Abstract Full Text Show Details

The following polyfunctional organic compounds are particularly preferred for the purposes of the present invention: 2,4,6-tris(4--hydroxyphenyl)amino-s-triazine; 3,7-dihydroxy-β-naphthoic acid; 1,3,5-trihydroxybenzene; 4,4--methylenebis(3-hydroxy-2-carboxynaphthalene); tris(4-hydroxyphenyl)methane; ...

Hide Experimental Procedure

ENICHEM S.p.A.

Patent: EP372623 A3, 1992 ; Title/Abstract Full Text Show Details

Polycarbonates as claimed in claim 1, characterised in that the dihydroxyaromatic compound (2) is chosen from: ... 3,7-dihydroxy-β-naphthoic acid; 1,3,5-trihydroxybenzene; 4,4--methylenebis(3-hydroxy-2-carboxynaphthalene); ...

Hide Experimental Procedure

ENICHEM S.p.A.

Patent: EP372623 A3, 1992 ; Title/Abstract Full Text Show Details

Process as claimed in claim 1, characterized in that the polyfunctional organic compound is chosen from: 2,4,6-tris(4--hydroxyphenyl)amino-s-triazine; 3,7-dihydroxy-β-naphthoic acid; 1,3,5-trihydroxybenzene; 4,4--methylenebis(3-hydroxy-2-carboxynaphthalene); tris(4-hydroxyphenyl)methane; ...

Synthesize Find similar

83%

With bis(trimethylsilyl)-sulfide; sodium methylate in various solvent(s) T=185°C; 24 h;

Synthesize Find similar

Rx-ID: 1716761 Find similar reactions

Hwu, Jih Ru; Tsay, Shwu-Chen

Journal of Organic Chemistry, 1990 , vol. 55, # 24 p. 5987 - 5991 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2045397 Find similar reactions

With sodium hydrogencarbonate; sodium sulfite in methanol; water

T=25°C; 0.25 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Kiehlmann, E.; Lauener, R. W.

Canadian Journal of Chemistry, 1989 , vol. 67, p. 335 - 344 Title/Abstract Full Text Show Details

Synthesize Find similar Rx-ID: 2106893 Find similar reactions

With bromine

1.) CS2, 80 min, 25 deg C; 2.) water, 70 deg C; Multistep reaction;

Synthesize Find similar

Kiehlmann, E.; Lauener, R. W.

Canadian Journal of Chemistry, 1989 , vol. 67, p. 335 - 344 Title/Abstract Full Text Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2193952 Find similar reactions

A: 8.5% B: 10.1%

With sodium tetrahydroborate in ethanol

Product distribution;

Funatsu, Takakazu; Iriye, Ryozo; Takai, Hideyuki; Hirota, Mitsuru

Agricultural and Biological Chemistry, 1989 , vol. 53, # 11 p. 3087 - 3090 Title/Abstract Full Text Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2211234 Find similar reactions

A: 7.5% B: 6% C: 6%

With sodium tetrahydroborate in ethanol

Product distribution;

Funatsu, Takakazu; Iriye, Ryozo; Takai, Hideyuki; Hirota, Mitsuru

Agricultural and Biological Chemistry, 1989 , vol. 53, # 11 p. 3087 - 3090 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 3385231 Find similar reactions

With acetic acid in ethanol

T=95°C; 1 h; Product distribution;

Foo, Lai Yeap; Karchesy, Joseph J.

Phytochemistry (Elsevier), 1989 , vol. 28, # 11 p. 3185 - 3190 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3385232 Find similar reactions

With acetic acid in ethanol

T=95°C; 1 h; Product distribution;

Foo, Lai Yeap; Karchesy, Joseph J.

Phytochemistry (Elsevier), 1989 , vol. 28, # 11 p. 3185 - 3190 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Rx-ID: 3385233 Find similar reactions

With acetic acid in ethanol

T=95°C; 1 h; Product distribution;

Synthesize Find similar

Foo, Lai Yeap; Karchesy, Joseph J.

Phytochemistry (Elsevier), 1989 , vol. 28, # 11 p. 3185 - 3190 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 3028588 Find similar reactions

alkali fusion;

Young, Esme; Brandt, Edward V.; Young, Desmond A.; Ferreira, Daneel; Roux, David G.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 1737 - 1750 Title/Abstract Full Text Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2127297 Find similar reactions

With potassium hydroxide

Chauhan, J. S.; Kumar, Santosh; Chaturvedi, Rajesh

Phytochemistry (Elsevier), 1984 , vol. 23, # 10 p. 2404 - 2405 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 483649 Find similar reactions

With potassium hydroxide

T=130°C; 1.5 h;

Sagareishvili, T. G.; Alaniya, M. D.; Kemertelidze, E. P.

Chemistry of Natural Compounds, 1983 , vol. 19, # 3 p. 275 - 278 Khimiya Prirodnykh Soedinenii, 1983 , vol. 19, # 3 p. 289 - 293 Title/Abstract Full Text View citing articles Show Details

durch Kalischmelze;

Perkin; Hummel

Journal of the Chemical Society, 1896 , vol. 69, p. 1291 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2159043 Find similar reactions

With potassium hydroxide

1.5 h; Heating;

Sagareishvili, T. G.; Alaniya, M. D.; Kikoladze, V. S.; Kemertelidze, E. P.

Chemistry of Natural Compounds, 1982 , vol. 18, # 4 p. 408 - 412 Khimiya Prirodnykh Soedinenii, 1982 , # 4 p. 442 - 446 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 123914 Find similar reactions

With potassium carbonate

beim Schmelzen;

Baeyer

Chemische Berichte, 1885 , vol. 18, p. 3457 Full Text View citing articles Show Details

With potassium hydroxide

T=100°C; 2.5 h; labelled comp.; Yield given;

Fujita, Masao; Inoue, Takao

Chemical & Pharmaceutical Bulletin, 1980 , vol. 28, # 8 p. 2482 - 2486 Title/Abstract Full Text Show Details

Synthesize

Find similar

With potassium hydroxide; sodium hydroxide

T=290 - 300°C; 1 h; labelled comp.;

Find similar

Rx-ID: 2166423 Find similar reactions

Fujita, Masao; Inoue, Takao

Chemical & Pharmaceutical Bulletin, 1980 , vol. 28, # 8 p. 2482 - 2486 Title/Abstract Full Text Show Details

Synthesize Find similar

With potassium hydroxide; sodium hydroxide

T=250 - 270°C; 3 h; labelled comp.; Yield given;

Synthesize Find similar

Rx-ID: 3207745 Find similar reactions

Fujita, Masao; Inoue, Takao

Chemical & Pharmaceutical Bulletin, 1980 , vol. 28, # 8 p. 2476 - 2481 Title/Abstract Full Text Show Details

Synthesize Find similar

Multi-step reaction with 2 steps 1: HI (d=1.7) / 2.5 h / Heating; labelled comp. 2: KOH-NaOH / 1 h / 290 - 300 °C / labelled comp. View Scheme

Synthesize Find similar

Rx-ID: 20133866 Find similar reactions

Fujita, Masao; Inoue, Takao

Chemical & Pharmaceutical Bulletin, 1980 , vol. 28, # 8 p. 2482 - 2486 Title/Abstract Full Text Show Details

Synthesize Find similar

Synthesize Find similar Fiege et al.

Ullmann, 1979 , vol. 18, p. 223 Full Text Show Details

Rx-ID: 283378 Find similar reactions

Synthesize Find similar

Rx-ID: 25330431 Find similar reactions

in isopropyl-benzene

Hide Experimental Procedure

Synthesize Find similar

Givaudan Corporation

Patent: US4112003 A1, 1978 ; Title/Abstract Full Text Show Details

4:EXAMPLE 4

3 g of triacetic acid lactone 3-O-benzyl ether are suspended, together with 2.9 g (4 equivalents) of lithium ethylate, in 60 ml of cumene and the mixture is refluxed for 4 hours. The mixture is then worked-up according to the procedure described in part (a) of Example 1. There are obtained 1.5 g of viscous phloroglucinol monoethyl ether (71percent of theory) which can be hydrolyzed to give phloroglucinol according to the procedure described in part (b) of Example 1. The conversion of the aforementioned propargyl ether into phloroglucinol can likewise be carried out according to the procedure described in part (b) of Example 1.

Synthesize Find similar

in hydrogenchloride

Hide Experimental Procedure

Synthesize Find similar

Rx-ID: 25348342 Find similar reactions

Givaudan Corporation

Patent: US4112003 A1, 1978 ; Title/Abstract Full Text Show Details

1.b:EXAMPLE 1

(b) 2 g of phloroglucinol monoethyl ether are stirred in 100 ml of concentrated hydrochloric acid (35percent) at room temperature for 2 days. The mixture is then partially neutralised (pH 2-3) with aqueous sodium carbonate solution, the precipitated sodium chloride is filtered off and the filtrate is extracted with 150 ml of ether in a Kutscher-Steudel extractor for 18 hours. The ether extract is dried over sodium sulphate and concentrated, there being obtained 1.4 g to 1.55 g (86percent to 95percent) of phloroglucinol which has a melting point of 209°-210° C. after recrystallisation from water. The triacetic acid δ-lactone methyl ether used as the starting material is prepared as follows:

Synthesize Find similar

Rx-ID: 8021580 Find similar reactions

Diaethylmalonat, Diaethyl<2-14C>malonat;

Gupta; Lewis

Journal of the Chemical Society [Section] C: Organic, 1971 , p. 629 Full Text Show Details

Malonsaeurediethylester-2-14C, Na (>Phloroglucindicarbonsaeurediethylester(2,4,6-14C); Verseifung+ Decarboxylierung;

Johne et al.

Pharmazie, 1970 , vol. 25, p. 777,779 Full Text Show Details

Synthesize Find similar

Rx-ID: 112311 Find similar reactions

Synthesize Find similar

Dressler

Kirk-Othmer, 1968 , vol. 16, p. 201,203 Full Text Show Details

Synthesize Find similar

aus Phloroglucin;

Rx-ID: 8030300 Find similar reactions

Massicot

Bulletin de la Societe Chimique de France, 1967 , p. 2204 Full Text Show Details

Synthesize Find similar

Rx-ID: 8031998 Find similar reactions

Severin,T.; Bohn,M.

Chemische Berichte, 1967 , vol. 100, # 1 p. 211 - 216 Full Text View citing articles Show Details

Phloroglucin mit NaOD;

Synthesize Find similar

Rx-ID: 6502242 Find similar reactions

Boecker

Ullmann, 1962 , vol. 13, p. 439 Full Text Show Details

Kaplan

Kirk-Othmer, 1953 , vol. 10, p. 388 Full Text Show Details

Synthesize Find similar

1.16%

other Radiation; neutron irradiation for 20 week long at room temp.;

Synthesize Find similar

Rx-ID: 26311852 Find similar reactions

Tanaka, Y. G.; Asami, Y.

Sci. Papers Inst. Phys. Chem. Res. (Tokyo), 1960 , vol. 54, p. 150 - 154 Full Text Show Details

Gmelin Handbook: C: MVol.D1, 39.7.2, page 379 - 379 Full Text Show Details

Synthesize Find similar Rx-ID: 5488013 Find similar reactions

T=150°C; Ausschluss von Sauerstoff;

Synthesize Find similar

Mayer; Bauni

Justus Liebigs Annalen der Chemie, 1958 , vol. 611, p. 264,267 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 293822 Find similar reactions

With sodium amalgam; water

unter Wasserstoff auf dem Dampfbad;

Posternak

Helvetica Chimica Acta, 1936 , vol. 19, p. 1333,1341 Helvetica Chimica Acta, 1946 , vol. 29, p. 1991,1996, 1997 Full Text View citing articles Show Details

With water; platinum

T=50 - 55°C; Hydrogenation;

Kuhn; Quadbeck; Roehm

Justus Liebigs Annalen der Chemie, 1949 , vol. 565, p. 1,5 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 7155018 Find similar reactions

T=50°C; Hydrogenation;

Synthesize Find similar

Kuhn; Quadbeck; Roehm

Justus Liebigs Annalen der Chemie, 1949 , vol. 565, p. 1,5 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 7155016 Find similar reactions

T=350°C;

Synthesize Find similar

Meijer

Recueil des Travaux Chimiques des Pays-Bas, 1946 , vol. 65, p. 843,848 Full Text Show Details

Synthesize Find similar

Rx-ID: 6502243 Find similar reactions

With ethanol

Erwaermen des Reaktionsgemisches, zuletzt auf dem Dampfbad;

Synthesize Find similar

McElvain; Langston

Journal of the American Chemical Society, 1943 , vol. 65, p. 2239,2240 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 7977240 Find similar reactions

anschliessend Erwaermen;

Synthesize Find similar

McElvain; Langston

Journal of the American Chemical Society, 1943 , vol. 65, p. 2239,2240 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 121023 Find similar reactions

Synthesize Find similar

T=200 - 220°C;

Prey

Chemische Berichte, 1941 , vol. 74, p. 1219,1221 Chemische Berichte, 1942 , vol. 75, p. 350,355, 356, 540 Full Text View citing articles Show Details

T=200 - 220°C;

Prey

Chemische Berichte, 1941 , vol. 74, p. 1219,1221 Chemische Berichte, 1942 , vol. 75, p. 350,355, 356, 540 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 266703 Find similar reactions

Synthesize Find similar

Brockmann; Maier

Justus Liebigs Annalen der Chemie, 1938 , vol. 535, p. 149,170 Justus Liebigs Annalen der Chemie, 1939 , vol. 541, p. 53,66 Anm. 1 Full Text View citing articles Show Details

Heller

Chemische Berichte, 1912 , vol. 45, p. 2389 Anm. 2 Chemische Berichte, 1915 , vol. 48, p. 1287 Full Text Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 5678947 Find similar reactions

T=150 - 160°C;

Synthesize Find similar

McGookin et al.

Journal of the Chemical Society, 1937 , p. 748,754 Journal of the Chemical Society, 1939 , p. 1579,1585 Full Text View citing articles Show Details

Synthesize Find similar

With sodium amalgam; water

unter Wasserstoff auf dem Dampfbad;

Synthesize Find similar

Rx-ID: 308302 Find similar reactions

Posternak

Helvetica Chimica Acta, 1936 , vol. 19, p. 1333,1341 Helvetica Chimica Acta, 1946 , vol. 29, p. 1991,1996, 1997 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 7155021 Find similar reactions

Synthesize Find similar

Posternak

Helvetica Chimica Acta, 1936 , vol. 19, p. 1333,1341 Helvetica Chimica Acta, 1946 , vol. 29, p. 1991,1996, 1997 Full Text View citing articles Show Details

Synthesize

Find similar Rx-ID: 7458087 Find similar reactions

Wasserstoff-Strom;

Find similar

Posternak

Helvetica Chimica Acta, 1936 , vol. 19, p. 1333,1341 Helvetica Chimica Acta, 1946 , vol. 29, p. 1991,1996, 1997 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 7920550 Find similar reactions

Goris; Canal

Bulletin de la Societe Chimique de France, 1936 , vol. <5> 3, p. 1982,1983, 1990 Full Text Show Details

Synthesize Find similar

Multi-step reaction with 2 steps 1: aqueous methanol. HCl 2: sodium-amalgam; water / unter Wasserstoff auf dem Dampfbad View Scheme

Synthesize Find similar

Rx-ID: 22085295 Find similar reactions

Posternak

Helvetica Chimica Acta, 1936 , vol. 19, p. 1333,1341 Helvetica Chimica Acta, 1946 , vol. 29, p. 1991,1996, 1997 Full Text View citing articles Show Details

Synthesize

Rx-ID: 341719

Find similar

With potassium hydroxide

T=250 - 270°C;

Find similar

Find similar reactions

Lock

Chemische Berichte, 1933 , vol. 66, p. 1759,1764 Full Text View citing articles Show Details

Synthesize Find similar

T=250 - 270°C;

Synthesize Find similar

Rx-ID: 7155017 Find similar reactions

Lock

Chemische Berichte, 1933 , vol. 66, p. 1759,1764 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 400215 Find similar reactions

In der Kalischmelze;

Brooks

Philippine J. Sci., 1910 , vol. <A> 5, p. 451 Chem. Zentralbl., 1911 , vol. 82, # II p. 649 Full Text Show Details

Cazeneuve; Hugounenq

Annales de Chimie (Cachan, France), 1889 , vol. <6> 17, p. 120 Full Text View citing articles Show Details

Dieterle; Leonhardt

Archiv der Pharmazie (Weinheim, Germany), 1929 , p. 104 Full Text View citing articles Show Details

Synthesize Find similar Rx-ID: 403610 Find similar reactions

Synthesize Find similar

bei der Kalischmelze;

Hattori

Acta Phytochimica, 1928 , vol. 4, p. 222 Chem. Zentralbl., 1929 , vol. 100, # I p. 761 Full Text View citing articles Show Details

bei der Kalischmelze;

Hattori

Chem. Zentralbl., 1929 , vol. 100, # II p. 1803 Full Text Show Details

Synthesize Find similar

T=180°C; (-)-epicatechol;

Synthesize Find similar

Rx-ID: 5434403 Find similar reactions

Tsujimura

Scientific Papers of the Institute of Physical and Chemical Research (Japan), vol. 10, p. 253,256 Chemisches Zentralblatt, 1929 , p. II, 1015 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 5700951 Find similar reactions

Perkin,A. G.

Journal of the Chemical Society, 1897 , vol. 71, p. 809 Full Text View citing articles Show Details

Schmid; Waschkau

Monatshefte fuer Chemie, 1928 , vol. 49, p. 85,87 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 586105 Find similar reactions

Synthesize Find similar

Karrer; Widmer

Helvetica Chimica Acta, 1927 , vol. 10, p. 7,20 Helvetica Chimica Acta, 1927 , vol. 10, p. 32 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 589587 Find similar reactions

Kochen mit Barytwasser;

Karrer; Widmer

Helvetica Chimica Acta, 1927 , vol. 10, p. 7,20 Helvetica Chimica Acta, 1927 , vol. 10, p. 32 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 573718 Find similar reactions

T=105 - 110°C;

Pollak; Gebauer-Fuelnegg

Monatshefte fuer Chemie, 1926 , vol. 47, p. 549 Full Text Show Details

Synthesize Find similar

Rx-ID: 706844 Find similar reactions

Pollak; Gebauer-Fuelnegg

Monatshefte fuer Chemie, 1926 , vol. 47, # 547 p. 548 Full Text Show Details

Synthesize Find similar

Rx-ID: 8145101 Find similar reactions

Pollak; Gebauer-Fuelnegg

Monatshefte fuer Chemie, 1926 , vol. 47, p. 549 Full Text Show Details

Synthesize Find similar

T=250 - 280°C; bei der Kalischmelze;

Synthesize Find similar

Rx-ID: 504625 Find similar reactions

Pollak; Gebauer-Fuelnegg; Blumenstock

Monatshefte fuer Chemie, 1925 , vol. 46, p. 505 Full Text Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 5690865 Find similar reactions

T=220 - 240°C;

Perkin

Journal of the Chemical Society, 1893 , vol. 63, p. 981 Journal of the Chemical Society, 1899 , vol. 75, p. 829 Full Text View citing articles Show Details

Dutt

Journal of the Chemical Society, 1925 , vol. 127, p. 2051 Full Text Show Details

Synthesize Find similar

Rx-ID: 5802175 Find similar reactions

Synthesize Find similar

Rennie; Cooke; Finlayson

Journal of the Chemical Society, 1920 , vol. 117, p. 348 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 745007 Find similar reactions

With calcium carbonate

Synthesize Find similar

Komninos

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1918 , vol. 167, p. 781

Bulletin de la Societe Chimique de France, 1918 , vol. <4> 23, p. 452 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 6211373 Find similar reactions

Synthesize Find similar

Komninos

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1918 , vol. 167, p. 781 Bulletin de la Societe Chimique de France, 1918 , vol. <4> 23, p. 452 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 6218121 Find similar reactions

Synthesize Find similar

Komninos

Synthesize Find similar

With water; calcium carbonate

Rx-ID: 6502240 Find similar reactions

Komninos

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1918 , vol. 167, p. 781 Bulletin de la Societe Chimique de France, 1918 , vol. <4> 23, p. 452

Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 6801276 Find similar reactions

Synthesize Find similar

Komninos

Synthesize Find similar

T=140°C;

Synthesize Find similar

Rx-ID: 7977241 Find similar reactions

Willstaetter; Burdick

Justus Liebigs Annalen der Chemie, 1917 , vol. 412, p. 217,224 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 7446969 Find similar reactions

beim Kochen;

Hoesch

Chemische Berichte, 1915 , vol. 48, p. 1125 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 7977603 Find similar reactions

Willstaetter; Mallison

Justus Liebigs Annalen der Chemie, 1915 , vol. 408, p. 36 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 7977604 Find similar reactions

T=210 - 250°C;

Willstaetter

Chem. Zentralbl., 1914 , vol. 85, # II p. 1356 Full Text Show Details

Willstaetter; Mallison

Justus Liebigs Annalen der Chemie, 1915 , vol. 408, p. 36 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 8212044 Find similar reactions

T=115 - 120°C;

Curtius

Journal fuer Praktische Chemie (Leipzig), 1915 , vol. <2> 91, p. 67 Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 8265299 Find similar reactions

Willstaetter; Bolton

Justus Liebigs Annalen der Chemie, 1915 , vol. 408, p. 59 Full Text View citing articles Show Details

Willstaetter

Chem. Zentralbl., 1914 , vol. 85, # II p. 1358 Full Text Show Details