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References
1
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Rx-ID: 39765357 Find similar reactions
61%
Stage #1: With trichlorophosphate
T=0 - 100°C; 1 h; Stage #2: With sodium acetate
T=100°C; 0.75 h; Hide Experimental Procedure
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Institute of Chemistry, Chinese Academy of Sciences; Wang, Meixiang; Wang, Dexian; He, Ling
Patent: CN104788462 B, 2017 ; Location in patent: Paragraph 0211; 0212; 0213 ; Title/Abstract Full Text Show Details
13:
100mL round bottom flask was added sesamol (4.1g, 30mmol)And DMF (24 mL) were completely dissolved and then cooled at 0 ° C under ice-cooling,POCl3 (16 mL) was slowly added dropwise.Drop finished,The reaction temperature was raised to 100 ° C,And the reaction was continued at this temperature for 1 hour.After cooling,The reaction mixture was poured into 250 mL of saturated sodium acetate solution,Heated to 100 ° C for 45 minutes,After cooling,The addition of dichloromethane (100 mL x 3 times)Organic saturated brine (100 mL x 3 times)Dried over anhydrous sodium sulfate,The solvent was removed by filtration under reduced pressure,100-200 mesh silica gel column chromatography,Ethyl acetate and petroleum ether mixed solvent (1:20)To give 3.0 g of the compound represented by the formula IIm,Yield 61percent. 11%
Stage #1: With trichlorophosphate
T=0 - 100°C; Vilsmeier-Haack Formylation; Stage #2: With sodium acetate
T=100°C;
Zhang, Bingyu; Lv, Chao; Li, Weibo; Cui, Zhiming; Chen, Dongdong; Cao, Fangjun; Miao, Fang; Zhou, Le
Chemical and Pharmaceutical Bulletin, 2015 , vol. 63, # 4 p. 255 - 262 Title/Abstract Full Text View citing articles Show Details
2
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Rx-ID: 11213602 Find similar reactions
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64%
With triethylamine; magnesium chloride in acetonitrile
T=125°C; 12 h; Sealed tube;
Sun, Peng; Gao, Shang; Yang, Chi; Guo, Songjin; Lin, Aijun; Yao, Hequan
Organic Letters, 2016 , vol. 18, # 24 p. 6464 - 6467 Title/Abstract Full Text View citing articles Show Details
45%
With triethylamine; magnesium chloride in tetrahydrofuran
Inert atmosphereReflux; regioselective reaction;
Akselsen, yvind W.; Skattebol, Lars; Hansen, Trond Vidar
Tetrahedron Letters, 2009 , vol. 50, # 46 p. 6339 - 6341 Title/Abstract Full Text View citing articles Show Details
36%
With triethylamine; magnesium chloride in tetrahydrofuran
2 h; Heating;
Juhasz, Laszlo; Docsa, Tibor; Brunyaszki, Attila; Gergely, Pal; Antus, Sandor
Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 12 p. 4048 - 4056 Title/Abstract Full Text View citing articles Show Details
26%
With triethylamine; magnesium chloride in acetonitrile
6 h; RefluxInert atmosphere;
Fowler, Katherine J.; Ellis, Jillian L.; Morrow, Gary W.
Synthetic Communications, 2013 , vol. 43, # 12 p. 1676 - 1682 Title/Abstract Full Text View citing articles Show Details
3
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Rx-ID: 4616206 Find similar reactions
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65%
With trifluoroacetic acid in dichloromethane
Duff formylation; Heating;
Bailly, Fabrice; Queffelec, Clemence; Mbemba, Gladys; Mouscadet, Jean-Francois; Cotelle, Philippe
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 22 p. 5053 - 5056 Title/Abstract Full Text View citing articles Show Details
56%
With trifluoroacetic acid
4 h; Heating;
Saito, Naoki; Tashiro, Kyoichi; Maru, Yukie; Yamaguchi, Kentaro; Kubo, Akinori
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1997 , # 1 p. 53 - 70 Title/Abstract Full Text Show Details
54%
With trifluoroacetic acid
Duff Aldehyde Synthesis; 3 h; RefluxInert atmosphere;
Guo, Wengang; Wu, Bo; Zhou, Xin; Chen, Ping; Wang, Xu; Zhou, Yong-Gui; Liu, Yan; Li, Can
Angewandte Chemie - International Edition, 2015 , vol. 54, # 15 p. 4522 - 4526 Angew. Chem., 2015 , vol. 127, # 15 p. 4605 - 4609,5 Title/Abstract Full Text View citing articles Show Details
53%
With trifluoroacetic acid
Duff Aldehyde Synthesis; 4 h; RefluxInert atmosphere; Hide Experimental Procedure
Jin, Yifeng; Khadka, Daulat Bikram; Yang, Su Hui; Zhao, Chao; Cho, Won-Jea
Tetrahedron Letters, 2014 , vol. 55, # 7 p. 1366 - 1369 Title/Abstract Full Text View citing articles Show Details
A solution of sesamol (12.5 g, 90.44 mmol) and hexamethylenetetramine(15.2 g, 108 mmol) in trifluoroacetic acid (50 mL) was heated under reflux for 4 h. The mixture was added to water (100 mL), extracted with CH2Cl2,and washed with water and brine. The organic phase was dried over sodiumsulfate and concentrated in vacuo.The resulting oil was purified by column chromatography with n-hexane-ethyl acetate (7:1) to afford compound 15 as white solid (7.94 g, 53percent). 1H NMR(300 MHz, CDCl3) δ: 11.78 (s, 1H), 9.62 (s, 1H), 6.86 (s, 1H), 6.46 (s, 1H), 6.02 (s, 2H). 45%
With trifluoroacetic acid
2 h; Heating;
Gagey, Nathalie; Neveu, Pierre; Benbrahim, Chouaha; Goetz, Bernard; Aujard, Isabelle; Baudin, Jean-Bernard; Jullien, Ludovic
Journal of the American Chemical Society, 2007 , vol. 129, # 32 p. 9986 - 9998 Title/Abstract Full Text View citing articles Show Details
45%
With trifluoroacetic acid
2 h; Reflux;
Gagey, Nathalie; Emond, Matthieu; Neveu, Pierre; Benbrahim, Chouaha; Goetz, Bernard; Aujard, Isabelle; Baudin, Jean-Bernard; Jullien, Ludovic
Organic Letters, 2008 , vol. 10, # 12 p. 2341 - 2344 Title/Abstract Full Text View citing articles Show Details
4
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With boron tribromide in dichloromethane
T=20°C; 10 h; Inert atmosphere; Hide Experimental Procedure
Rx-ID: 5451175 Find similar reactions
COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; VISHWAKARMA, Ram Asrey; SAWANT, Sanghapal Damodhar; SINGH, Parvinder Pal; DAR, Abid Hamid; SHARMA, Parduman Raj; SAXENA, Ajit Kumar; NARGOTRA, Amit; KOLLURU, Anjaneya Aravind Kumar; MUDUDUDDLA, Ramesh; QAZI, Asif Khurshid; HUSSAIN, Aashiq; CHANAURIA, Nayan
Patent: WO2013/140417 A1, 2013 ; Location in patent: Page/Page column 19; 23 ; Title/Abstract Full Text Show Details
1:
General procedure: All the compounds disclosed in formula 1, are prepared by employing the similar method containing different substitutions at Rl, R2, R3 and R4 positions, as described for the preparation of compound A. The details of reaction conditions are depicted in the table given below-; Step 1; Synthesis of 2-hvdroxy. 4.5-dimethoxybenzaldehyde (Al): To solution of 3,4,5- trimethoxybenzaldehyde (5g, 25.5 mmol) in CH2C12 (125 ml) at 0 °C was added BBr3 (6.39 g, 25.5 mmol). The resulting dark mixture was stirred at 0°C for 10 hrs after completion of the reaction checked by TLC H20 (100 mL) was then added and the mixture was stirred for 10 min and the aqueous phase was extracted by CH2C12. The organic phase was dried over Na2S0 ) and evaporated under reduced pressure. The resulting residue was purified by silica gel (CH C12) afforded the 2- hydroxy 4,5dimethoxybenzaldehyde Al (4.3g) in 87percent yield isolated yellow solid: lH NMR (500 MHz, CDC13) 511.33 (s, 1H), 9.63 (s, 1H), 6.83 (s, 1H), 6.40 (s, 1H), 3.87 (s, 3H), 3.81 (s, 3H) ppm. Mass: ESI [M + Na]+: 225.06; Elemental anal, calcd. for C9H10O4; C: 59.34, H: 5.53, O: 35.13; found C: 59.14, H: 5.13, O: 34.90.
84%
With boron tribromide in dichloromethane
T=20°C; 10 h; Inert atmosphere; Hide Experimental Procedure
Vishwakarma, Ram Asrey; Sawant, Sanghapal Damodhar; Singh, Parvinder Pal; Dar, Abid Hamid; Sharma, Parduman Raj; Saxena, Ajit Kumar; Nargotra, Amit; Kolluru, Anjaneya Aravind Kumar; Mudududdla, Ramesh; Qazi, Asif Khurshid; Hussain, Aashiq; Chanauria, Nayan
Patent: US2015/51173 A1, 2015 ; Location in patent: Paragraph 0114; 0123 ; Title/Abstract Full Text Show Details
1:Synthesis of Compound A Step 1 Synthesis of 2-hydroxy, 4,5-dimethoxybenzaldehyde (A1)
General procedure: Synthesis of Compound A Step 1 Synthesis of 2-hydroxy-4,5-dimethoxybenzaldehyde (A1) To solution of 2,4,5-trimethoxybenzaldehyde (5 g, 25.5 mmol) in CH2Cl2 (125 ml) at 0° C. was added BBr3 (6.39 g, 25.5 mmol). The resulting dark mixture was stirred at 0° C. for 10 hrs after completion of the reaction checked by TLC H2O (100 mL) was then added and the mixture was stirred for 10 min and the aqueous phase was extracted by CH2Cl2. The organic phase was dried over Na2SO4, and evaporated under reduced pressure. The resulting residue was purified by silica gel (CH2Cl2) afforded the 2-hydroxy-4,5-dimethoxybenzaldehyde A1 (4.3 g) in 87percent yield isolated yellow solid. 35%
Takeda Chemical Industries, Ltd.
Hide Experimental Procedure
Patent: US5716944 A1, 1998 ; Title/Abstract Full Text Show Details
R.38:Reference Example 38 Reference Example 38 To a mixture of sesamol (8.28 g), ethyl orthoformate (53.58 g) and benzene (120 ml), powdered anhydrous aluminum chloride (12.0 g) was added, followed by stirring at room temperature for 1 hour. The mixture was then poured into 5percent hydrochloric acid (180 ml) and stirred at room temperature for 30 minutes. After the insoluble substance was filtered off, the filtrate was extracted with ether. The ether layer was washed with water and dried (MgSO4), after which the solvent was evaporated off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:8, v/v) to yield 2-hydroxy-4,5-methylenedioxybenzaldehyde (3.48 g, 35percent) having a melting point of 128°-129° C.
Suginome,H.
Bulletin of the Chemical Society of Japan, 1966 , vol. 39, p. 1525 - 1529 Full Text View citing articles Show Details
van Heerden,F.R. et al.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1978 , p. 137 - 145 Full Text View citing articles Show Details
Fukui; Nakayama
Bulletin of the Chemical Society of Japan, 1962 , vol. 35, p. 1321 Full Text Show Details
PHARMACIA CORPORATION
Patent: WO2004/87686 A2, 2004 ; Location in patent: Page 272-273 ; Title/Abstract Full Text Show Details
PHARMACIA CORPORATION
Patent: WO2004/87687 A1, 2004 ; Location in patent: Page 272-273 ; Title/Abstract Full Text Show Details
5
Synthesize Find similar Multi-step reaction with 3 steps 1.1: nitric acid / water / 0.5 h / 20 °C 2.1: iron(II) sulfate; ammonium hydroxide / water / 0.17 h / |Heating 3.1: sodium nitrite; sulfuric acid / water / 5 °C 3.2: 8 h / 100 °C View Scheme
6
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Rx-ID: 40920967 Find similar reactions
De Melos, Jorge Luiz R.; Torres-Santos, Eduardo Caio; Faiões, Viviane Dos S.; De Nigris Del Cistia, Catarina; Sant'Anna, Carlos Maurício R.; Rodrigues-Santos, Cláudio Eduardo; Echevarria, Aurea
European Journal of Medicinal Chemistry, 2015 , vol. 103, p. 409 - 417 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar Multi-step reaction with 2 steps 1.1: iron(II) sulfate; ammonium hydroxide / water / 0.17 h / |Heating 2.1: sodium nitrite; sulfuric acid / water / 5 °C 2.2: 8 h / 100 °C View Scheme
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Rx-ID: 40920979 Find similar reactions
De Melos, Jorge Luiz R.; Torres-Santos, Eduardo Caio; Faiões, Viviane Dos S.; De Nigris Del Cistia, Catarina; Sant'Anna, Carlos Maurício R.; Rodrigues-Santos, Cláudio Eduardo; Echevarria, Aurea
European Journal of Medicinal Chemistry, 2015 , vol. 103, p. 409 - 417 Title/Abstract Full Text View citing articles Show Details
7
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Stage #1: With sulfuric acid; sodium nitrite in water
T=5°C; Stage #2: With water; copper(II) sulfate
T=100°C; Sandmeyer Reaction; 8 h;
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Rx-ID: 40920990 Find similar reactions
De Melos, Jorge Luiz R.; Torres-Santos, Eduardo Caio; Faiões, Viviane Dos S.; De Nigris Del Cistia, Catarina; Sant'Anna, Carlos Maurício R.; Rodrigues-Santos, Cláudio Eduardo; Echevarria, Aurea
European Journal of Medicinal Chemistry, 2015 , vol. 103, p. 409 - 417 Title/Abstract Full Text View citing articles Show Details
8
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Rx-ID: 10494775 Find similar reactions
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91%
With tin(IV) chloride in dichloromethane
T=0 - 20°C; 3 h;
Beekman, Andrew M.; Barrow, Russell A.
Journal of Organic Chemistry, 2014 , vol. 79, # 3 p. 1017 - 1024 Title/Abstract Full Text View citing articles Show Details
46%
With tin(IV) chloride in dichloromethane
Cueva, Juan Pablo; Giorgioni, Gianfabio; Grubbs, Russell A.; Chemel, Benjamin R.; Watts, Val J.; Nichols, David E.
T=20°C; 3 h;
Journal of Medicinal Chemistry, 2006 , vol. 49, # 23 p. 6848 - 6857 Title/Abstract Full Text View citing articles Show Details
40%
With tin(ll) chloride in dichloromethane
T=20°C; 3 h;
Fadeyi, Olugbeminiyi O.; Nathan Daniels; DeGuire, Sean M.; Lindsley, Craig W.
Tetrahedron Letters, 2009 , vol. 50, # 25 p. 3084 - 3087 Title/Abstract Full Text View citing articles Show Details
38%
With tin(IV) chloride in dichloromethane
T=0 - 20°C; Product distribution / selectivity; Hide Experimental Procedure
PURDUE RESEARCH FOUNDATION
Patent: US2009/30025 A1, 2009 ; Location in patent: Page/Page column 12 ; Title/Abstract Full Text Show Details
1:
Example 1 6-Hydroxybenzo[1,3]dioxole-5-carbaldehyde (2a). Sesamol (1a) (16.95 g, 1.23 mol) was dissolved in 350 ml CH2Cl2 in a two necked round bottom flask connected to a condenser. SnCl4 (35.4 ml, 3.07 mmol) was added and the solution was stirred at 0° C. Cl2CHOCH3 (11.7 ml, 1.29 mol) was added dropwise, and the solution was warmed to room temperature. The dark bluish mixture was cooled, and poured into a flask containing 500 ml of ice and water. The water layer was discarded, and the organic phase was filtered through Celite. The filtrates were washed with 2 M HCl (3*200 ml), and then with brine (1*100 ml). The solution was dried over MgSO4, filtered, and the solvent evaporated. The dark brown solids were then dissolved in ethanol, stirred with charcoal and filtered through Celite. Solvent was evaporated and the product was recrystallized from methanol to give 7.74 g (38percent yield): mp 119° C. This Example was repeated on a larger scale. Sesamol (50.98 g, 369 mmol) was dissolved in 600 mL of CH2Cl2 followed by 52 mL (448 mmol) of SnCl4 and the solution was cooled to 0° C. Cl2CHOCH3 (35 mL, 387.5 mmol) was added dropwise as the reaction mixture warmed to room temperature, and was then stirred for 3 h. The mixture was poured over ice, the water layer was separated and extracted once with CH2Cl2 (30 mL). The organic extracts were combined, washed with 2M HCl (5*100 mL), and brine (50 mL), and then passed through a small column packed with MgSO4, which removed color. The solvent was evaporated to yield 28 g (46percent yield): mp 119° C.; 1H-NMR (CDCl3) δ 9.63 (s, 1, CHO); 6.87 (s, 1, ArH); 6.47 (s, 1, ArH); 6.02 (s, 2, ArOCH2O); 1.54 (s, 1, ArOH); low resolution CIMS: m/z (rel. intensity) 167 (MH+, 100). Anal. Calcd. for C8H6O4: C, 57.84; H, 3.64. Found: C, 57.65; H, 3.76.
9
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10
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Rx-ID: 1728435 Find similar reactions
Vilsmeier reaction;
Ohishi; Mukai; Nagahara; Yajima; Kajikawa
Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 9 p. 2398 - 2405 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / Cooling with ice 1.2: 3 h / 20 °C / Cooling with ice 2.1: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme
Cueva, Juan Pablo; Chemel, Benjamin R.; Juncosa Jr., Jose I.; Lill, Markus A.; Watts, Val J.; Nichols, David E.
European Journal of Medicinal Chemistry, 2012 , vol. 48, p. 97 - 107 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 32585192 Find similar reactions
93.2%
With tin(IV) chloride in dichloromethane
T=0°C; Friedel-Crafts type formylation; 2 h; Hide Experimental Procedure
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Cueva, Juan Pablo; Chemel, Benjamin R.; Juncosa Jr., Jose I.; Lill, Markus A.; Watts, Val J.; Nichols, David E.
European Journal of Medicinal Chemistry, 2012 , vol. 48, p. 97 - 107 Title/Abstract Full Text View citing articles Show Details
4.2.3. 6-Hydroxybenzo[1,3]dioxole-5-carboxaldehyde (10)
In a two-neck flask, 40 g of 9 (0.222 mol) were dissolved in 500 mL CH2Cl2 and the solution cooled to 0 °C. Through a dropping funnel, 52 mL (0.444 mol) of SnCl4 were added dropwise, followed by slow addition of 22 mL (0.244 mol) of Cl2CHOCH3, causing the formation of a precipitate. The reaction was stirred for 2 h and was then poured over ice. The mixture was partitioned and the organic layer was washed with of 2M HCl (3 .x. 20 mL), and then with water (2 .x. 50 mL). The organic solution was dried over Na2SO4, filtered, and the solvent removed by rotary evaporation to afford a solid, which was triturated under cold MeOH, filtered, and dried to yield 34.38 g (93.2percent) of 10 as a tan solid: mp 120-121 °C (Lit [28]. mp 125-126). 1H NMR (CDCl3): δ 9.63 (s, 1H, CHO), 6.87 (s, 1H, ArH), 6.47 (s, 1, ArH), 6.02 (s, 2H, ArOCH2O), 1.54 (s, 1H, ArOH). CIMS: m/z 167 (M + H+, 100). Anal. (C8H6O4) C, H. A
B
C
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11
Synthesize Find similar Rx-ID: 33309727 Find similar reactions
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 5 h / Reflux; Inert atmosphere 2: 1.5 h / 180 °C / Inert atmosphere; Neat (no solvent) 3: potassium tert-butylate / dimethyl sulfoxide / 1.5 h / 100 °C / Inert atmosphere 4: oxygen; 4-methoxy-2,2,6,6-tetramethylpiperidine-1oxy / benzene / 4 h / 70 °C View Scheme
Constantin, Mihaela-Anca; Conrad, Juergen; Merisor, Elena; Koschorreck, Katja; Urlacher, Vlada B.; Beifuss, Uwe
Journal of Organic Chemistry, 2012 , vol. 77, # 10 p. 4528 - 4543 Title/Abstract Full Text View citing articles Show Details
A
12
B
C
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A: 18 %Spectr.
With oxygen; 4-methoxy-2,2,6,6tetramethylpiperidin-1-oxyl radical in benzene
T=70°C; 4 h; optical yield given as percent de;
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Constantin, Mihaela-Anca; Conrad, Juergen; Merisor, Elena; Koschorreck, Katja; Urlacher, Vlada B.; Beifuss, Uwe
Journal of Organic Chemistry, 2012 , vol. 77, # 10 p. 4528 - 4543 Title/Abstract Full Text View citing articles Show Details
A
B
C
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13
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Multi-step reaction with 3 steps 1: 1.5 h / 180 °C / Inert atmosphere; Neat (no solvent) 2: potassium tert-butylate / dimethyl sulfoxide / 1.5 h / 100 °C / Inert atmosphere 3: oxygen; 4-methoxy-2,2,6,6-tetramethylpiperidine-1oxy / benzene / 4 h / 70 °C View Scheme
Constantin, Mihaela-Anca; Conrad, Juergen; Merisor, Elena; Koschorreck, Katja; Urlacher, Vlada B.; Beifuss, Uwe
Journal of Organic Chemistry, 2012 , vol. 77, # 10 p. 4528 - 4543 Title/Abstract Full Text View citing articles Show Details
A
B
C
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14
Synthesize Find similar Rx-ID: 33309746 Find similar reactions
Multi-step reaction with 2 steps 1: potassium tert-butylate / dimethyl sulfoxide / 1.5 h / 100 °C / Inert atmosphere 2: oxygen; 4-methoxy-2,2,6,6-tetramethylpiperidine-1oxy / benzene / 4 h / 70 °C View Scheme
Constantin, Mihaela-Anca; Conrad, Juergen; Merisor, Elena; Koschorreck, Katja; Urlacher, Vlada B.; Beifuss, Uwe
Journal of Organic Chemistry, 2012 , vol. 77, # 10 p. 4528 - 4543 Title/Abstract Full Text View citing articles Show Details
15
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Rx-ID: 28856304 Find similar reactions
Stage #1: With hydrogenchloride; zinc(II) chloride in diethyl ether
T=20°C; Gattermann aldehyde synthesis; Stage #2: in diethyl ether
Gattermann aldehyde synthesis; 0.5 h; HeatingAcidic aq. solution;
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Riveiro, Maria E.; Maes, Dominick; Vazquez, Ramiro; Vermeulen, Monica; Mangelinckx, Sven; Jacobs, Jan; Debenedetti, Silvia; Shayo, Carina; De Kimpe, Norbert; Davio, Carlos
Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 18 p. 6547 - 6559 Title/Abstract Full Text View citing articles Show Details
16
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Rx-ID: 9869028 Find similar reactions
76%
Stage #1: With hydrogenchloride; sodium chloride; zinc(II) chloride in diethyl ether
T=20°C; Gattermann formylation; 0.5 h; Stage #2: With sulfuric acid in water
T=100°C; 0.5 h;
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Maes, Dominick; Vervisch, Stijn; Debenedetti, Silvia; Davio, Carlos; Mangelinckx, Sven; Giubellina, Nicola; De Kimpe, Norbert
Tetrahedron, 2005 , vol. 61, # 9 p. 2505 - 2511 Title/Abstract Full Text View citing articles Show Details
A
17
B
C
D
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Rx-ID: 9881434 Find similar reactions
A: 52% B: 3% C: 3% D: 18%
With copper dichloride in methanol; N,N-dimethylformamide
T=100°C; 32 h;
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Maes, Dominick; Vervisch, Stijn; Debenedetti, Silvia; Davio, Carlos; Mangelinckx, Sven; Giubellina, Nicola; De Kimpe, Norbert
Tetrahedron, 2005 , vol. 61, # 9 p. 2505 - 2511 Title/Abstract Full Text View citing articles Show Details
18
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Rx-ID: 23745193 Find similar reactions
70.9%
With AlCl3, aluminium chloride in diethyl ether
T=0°C; 0.0833333 h; Hide Experimental Procedure
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Kureha Chemical Industry Co., Ltd.
Patent: EP1357118 A1, 2003 ; Location in patent: Page/Page column 18 ; Title/Abstract Full Text Show Details
6:
To an eggplant type flask (100 mL), sesamol (1.38 g, 10.0 mmol, 1.0 equivalent) and ether (40 mL) were added and dissolved. Triethyl orthoformate (10 mL, 7.6 mmol, 7.6 equivalents) was added to the solution. To the resulting yellow solution, aluminum chloride (2.0 g, 15 mmol, 1.5 equivalents) was added portionwise at 0C. The mixture color was changed from light red to green, and further, from dark green to dark blue. After 5 minutes, the mixture was cooled to 0C, and a 5percent hydrochloric acid solution (10 mL) was added. The resulting product was slightly soluble, and the separation thereof was difficult. The separation was carried out by adding distilled water (1 0mL) and ethyl acetate (40 mL). The aqueous layer was further extracted with ethyl acetate (40 mL). The collected organic layer was washed with saturated brine (10 mL), dried over sodium sulfate (approximately 5 g), and concentrated and solidified by an evaporator to obtain a dark red solid (1.6 g). From the resulting dark red solid, 506.6 mg thereof was taken and purified by silica gel chromatography [2.5 (diameter) *8.0 cm, 20 g; n-hexane:ethyl acetate (3:1)] to obtain 4,5-methylenedioxysalicylaldehyde (363.9 mg, yield = 70.9percent) in Fraction Nos. 2-4 as light brown needle crystals. Melting point: 125-126C TLC: Rf = 0.63 (n-hexane/ethyl acetate = 2:1) 1H-NMR (CDCl , δ ppm): 6.02 (s, 6H, Me ), 6.47 (s, 1H), 6.86 (s, 1H), 9.62 (s, 1H, CHO) 3 2
IR (KBr cm-1): 3076, 1646, 1614, 1506, 1482, 1424, 1388, 1314, 1270, 1230, 1162, 1086, 1036, 934, 872, 854, 786, 774, 722, 710, 514
19
Synthesize Find similar Multi-step reaction with 2 steps 1: 10percent aq. KOH / methanol / 2.5 h / Ambient
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Rx-ID: 17370660 Find similar reactions
Saito, Naoki; Tashiro, Kyoichi; Maru, Yukie; Yamaguchi, Kentaro; Kubo, Akinori
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1997 , # 1 p. 53 - 70
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temperature 2: 56 percent / CF3COOH / 4 h / Heating View Scheme
Title/Abstract Full Text Show Details
20
Synthesize Find similar Multi-step reaction with 3 steps 1: m-CPBA / CH2Cl2 / 4 h / Heating 2: 10percent aq. KOH / methanol / 2.5 h / Ambient temperature 3: 56 percent / CF3COOH / 4 h / Heating View Scheme
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Rx-ID: 17371124 Find similar reactions
Saito, Naoki; Tashiro, Kyoichi; Maru, Yukie; Yamaguchi, Kentaro; Kubo, Akinori
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1997 , # 1 p. 53 - 70 Title/Abstract Full Text Show Details
21
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With aluminium trichloride; acetyl chloride in dichloromethane
T=-30°C; 0.5 h;
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Rx-ID: 2661811 Find similar reactions
Kelkar, Shriniwas L.; Phadke, Chetan P.; Marina, Sister
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984 , vol. 23, # 5 p. 458 - 459 Title/Abstract Full Text Show Details
A
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D
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22
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Rx-ID: 1576674 Find similar reactions
A: 3 mg
With lithium perchlorate
Nishiyama; Eto; Terada; et al.
B: 39 mg C: 169 mg D: 63 mg
anodic oxidation;
Chemical and Pharmaceutical Bulletin, 1983 , vol. 31, # 8 p. 2834 - 2844 Title/Abstract Full Text View citing articles Show Details
A
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C
D
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23
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Rx-ID: 1576673 Find similar reactions
A: 1% B: 11% C: 44% D: 15%
anodic oxidation;
Iguchi, Masanobu; Nishiyama, Atsuko; Eto, Hideo; Yamamura,Shosuke
Chemistry Letters, 1981 , p. 939 - 942 Title/Abstract Full Text Show Details
A
B
C
D
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24
Synthesize Find similar Rx-ID: 1747212 Find similar reactions
A: 1% B: 11% C: 44% D: 15%
in methanol
anodic oxidation;
Iguchi, Masanobu; Nishiyama, Atsuko; Eto, Hideo; Yamamura,Shosuke
Chemistry Letters, 1981 , p. 939 - 942 Title/Abstract Full Text Show Details
25
Synthesize Find similar
Rx-ID: 5451176 Find similar reactions
With copper(II) sulfate
Campbell et al.
Journal of Organic Chemistry, 1951 , vol. 16, p. 1736,1740 Full Text View citing articles Show Details
Arnold; Bordwell
Journal of the American Chemical Society, 1942 , vol. 64, p. 2983,2985 Full Text View citing articles Show Details