Reaxys
PubChem
eMolecules
Reactions (12)
Yield
Substances (3)
Citations (46)
Conditions
References
1
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Rx-ID: 597401 Find similar reactions
97%
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With [C4dabco]OH in neat (no solvent) T=20°C; Henry Nitro Aldol Condensation; 0.25 h; Green chemistry; Hide Experimental Procedure
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Keithellakpam, Sanjoy; Laitonjam, Warjeet S.
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016 , vol. 55B, # 1 p. 110 - 113 Title/Abstract Full Text View citing articles Show Details
General procedure for Henry reaction
General procedure: A general procedure for the Henry reaction is as follows: A 50 mL round bottomed flask was charged with the carbonyl compound (3 mmol), the nitroalkane (9 mmol) and ionic liquid catalyst [C4dabco]OH (0.168 g, 10 molpercent). The reaction mixture was stirred at RT. The formation of the product was monitored by TLC. After completion of the reaction, water (3 mL) and diethyl ether (5 mL) were added and the reaction mixture was separated into two layers. As IL was soluble in water, pure IL was obtained after evaporation of water under reduced pressure, which could be reused for subsequent reactions. Pure 2-nitroalcohol was obtained from the diethyl ether layer after distillation or column chromatography. All the products were previously reported and were characterized by melting point determination, IR, NMR spectroscopy and elemental analyses. Selected data for representative compounds are given below. 97%
With [C4dabco]OH in neat (no solvent) T=20°C; Henry Nitro Aldol Condensation; 0.25 h; Ionic liquidGreen chemistry;
Keithellakpam, Sanjoy; Laitonjam, Warjeet S.
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016 , vol. 55B, # 1 p. 110 - 113 Title/Abstract Full Text Show Details
95%
With tetrabutyl ammonium fluoride; tert-butyldimethylsilyl chloride; triethylamine in tetrahydrofuran
0.0833333 h;
Fernandez; Gasch; Gomez-Sanchez; Vilchez
Tetrahedron Letters, 1991 , vol. 32, # 27 p. 3225 - 3228 Title/Abstract Full Text View citing articles Show Details
93%
With potassium tert-butylate in tetrahydrofuran; water; tert-butyl alcohol
T=0 - 20°C; 16 h; Hide Experimental Procedure
Takeda Pharmaceutical Company Limited
Patent: EP2005957 A1, 2008 ; Location in patent: Page/Page column 46 ; Title/Abstract Full Text Show Details
6:2-nitro-1-phenylpropan-1-ol
Reference Example 6 2-nitro-1-phenylpropan-1-ol To a solution of benzaldehyde (20.0 g) and nitroethane (28.4 g) in tetrahydrofuran (50 mL) and tert-butanol (50 mL) was added potassium tert-butoxide (1.27 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1) to give the title compound as a blue oil (yield 32.0 g, 93percent). 1H-NMR (CDCl ) δ: 1.23-1.34 (3H, m), 2.56-2.70 (1H, m), 4.68-4.80 (1H, m), 5.01-5.42 (1H, m), 7.32-7.41 (5H, m). 3 91%
With C62H60N4O4P(1+)*Cl(1-); sodium t-butanolate in tetrahydrofuran T=-78°C; Henry Nitro Aldol Condensation; 0.5 h; Inert atmosphere; enantioselective reaction; Hide Experimental Procedure
Kunming University of Science and Technology; LIAO, XIALI; GAO, KAI; REN, YUFENG; YANG, BO; YANG, JIAN
Patent: CN104844654 B, 2016 ; Location in patent: Paragraph 0044-00047 ; Title/Abstract Full Text Show Details
The chiral quaternary salt catalyst provided by the present invention can be used for asymmetric Henry reaction,The reaction examples of the application examples are as followsunder:
The quaternary salt catalyst lb (13.75 μο1,0. 055 equiv) was added to a 10 mL reaction flask and dissolved in 2.5 mLTetrahydro-Sasmonium, argon protection,At room temperatureAdd nitro-ethyl burn(2.5 mmol, 10.0 equiv), 12.5 μη ο1Potassium tert-butoxide (1 M, tetrahydrofuran solution) was added to the reaction solution at -78 ° C and stirred for 30 minutes.Then benzaldehyde (0.25 mmo 1,1.0 equiν) was slowly added dropwise to the reaction.After completion of the reaction, trifluoroacetic acid was addedOf toluene solution (100 ymL, 0.5M), and then the reaction solution into ice water, the organic phase separation, the water phase to acetic acid BEster extraction, combined organic phase anhydrous magnesium sulfate dry,Column chromatography in a yield of 91percent.By high performance liquid chromatography, the corresponding selectivity was obtained98percent 90%
With potassium tert-butylate in tetrahydrofuran; tert-butyl alcohol
T=20°C; Henry reaction; 18.5 h;
Gorczynski, Michael J.; Huang, Jinming; Lee, Heather; King, S. Bruce
Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 7 p. 2013 - 2017 Title/Abstract Full Text View citing articles Show Details
89%
With potassium tert-butylate; tert-butyl alcohol in tetrahydrofuran; tert-butyl alcohol
T=0°C; 16 h;
Denmark, Scott E.; Kesler, Brenda S.; Moon, Young-Choon
Journal of Organic Chemistry, 1992 , vol. 57, # 18 p. 4912 - 4924 Title/Abstract Full Text View citing articles Show Details
89%
With 2-(2-boronophenyl)-N-n-butyl-benzimidazole in water
T=20°C; Henry Reaction; 72 h; Product distribution / selectivity; Hide Experimental Procedure
UNIVERSITY OF DURHAM
Patent: WO2004/113351 A2, 2004 ; Location in patent: Page 41-42 ; Title/Abstract Full Text Show Details
4.B1:B1 First general procedure for nitro aldol with nitroethane The aldehyde (1 mmol) was placed in a vial and nitroethane (0.6 ml) was added. The catalyst (14.7 mg; 0.05 mmol) was then added followed by water (0.9 ml). The resulting biphasic reaction mixture was then stirred for 3 days at room temperature. Water (0.5 ml) and DCM (1.0 ml) were then added and the liquor stirred for 10 minutes. The phases were then separated and the aqueous layer was further extracted with DCM (1 x LML). The combined organic extracts were then passed through a small plug of silica gel and magnesium sulfate, and evaporated under reduced pressure. The resulting residue analysed by proton NMR spectroscopy. 89%
With 2-(2-boronophenyl)-N-n-butyl-benzimidazole in tetrahydrofuran-d8; [D3]acetonitrile; water
T=20°C; Henry Reaction; 120 h; Product distribution / selectivity; Hide Experimental Procedure
UNIVERSITY OF DURHAM
Patent: WO2004/113351 A2, 2004 ; Location in patent: Page 41-42 ; Title/Abstract Full Text Show Details
4.B2:B2 Second general procedure for nitro aldol with nitroethane The catalyst (7.3 mg, 2.5 JUMOL) was placed in a vial and an aliquot of benzaldehyde solution was added (0.5 ml of a solution containing 0. 530 g in 5 ml of CD3CN ; 0.5 mmol). Deuterated THF (0.5 ml) was then added followed by nitroethane (179 ss 2.5 mmol). The appropriate amount of CD3CN and water were then added to take the total solvent volume to 2.5 ml. Each of the reaction solutions was then stirred at room temperature for 5 days. Water (1.0 ml) and DCM (1.0 ml) were then added and the liquor stirred for 10 minutes. The phases were then separated and the aqueous layer was further extracted with DCM (2 X lml). The combined organic extracts were then passed through a small plug of silica gel and magnesium sulfate, and evaporated under reduced pressure. The resulting residue analysed by proton NMR spectroscopy. 88%
With N-benzyl-trimethylammonium hydroxide in tetrahydrofuran; water
T=20°C; 0.1 h;
Bulbule; Jnaneshwara; Deshmukh; Borate; Deshpande
Synthetic Communications, 2001 , vol. 31, # 23 p. 3623 - 3626 Title/Abstract Full Text View citing articles Show Details
88%
With 1H-imidazole in water
T=20°C; Henry reaction; 0.5 h;
Phukan, Mridula; Jyoti Borah, Kalyan; Borah, Ruli
Synthetic Communications, 2008 , vol. 38, # 18 p. 3068 - 3073 Title/Abstract Full Text View citing articles Show Details
87%
With hydrotalcite in tetrahydrofuran
Condensation; Henry reaction; addition; 6 h; Heating;
Bulbule, Vivek J.; Deshpande, Vishnu H.; Velu, Subramani; Sudalai, Arumugam; Sivasankar; Sathe
Tetrahedron, 1999 , vol. 55, # 30 p. 9325 - 9332 Title/Abstract Full Text View citing articles Show Details
84%
With 4 A molecular sieve in dimethyl sulfoxide
T=20°C; Henry reaction; 24 h;
Oriyama, Takeshi; Aoyagi, Masaru; Iwanami, Katsuyuki
Chemistry Letters, 2007 , vol. 36, # 5 p. 612 - 613 Title/Abstract Full Text View citing articles Show Details
81%
With potassium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate
T=20°C; Henry reaction; 5 h;
Khan, Faiz Ahmed; Sudheer; Sahu, Nilam
Synthetic Communications, 2005 , vol. 35, # 2 p. 201 - 207 Title/Abstract Full Text View citing articles Show Details
75%
With silica gel in neat (no solvent) 0.0833333 h; Irradiation;
Kumar, H. M. Sampath; Reddy, B. V. Subba; Yadav, J. S.
Chemistry Letters, 1998 , # 7 p. 637 - 638 Title/Abstract Full Text Show Details
71%
With 2C10H7NO5(2-)*3CH3NO*H(1+)*Sm(3+) in water T=70°C; Henry Nitro Aldol Condensation; 36 h; Catalytic behavior; Reagent/catalystTemperatureSolventTime;
Karmakar, Anirban; Hazra, Susanta; Guedes Da Silva, M. Fátima C.; Paul, Anup; Pombeiro, Armando J. L.
CrystEngComm, 2016 , vol. 18, # 8 p. 1337 - 1349 Title/Abstract Full Text View citing articles Show Details
68%
With Mg-1,3-dimethylimidazolinium carbene complex immobilized on the nano-MgO surface in toluene
T=60°C; 12 h; Hide Experimental Procedure
Shaikh, Melad; Sahu, Mahendra; Gavel, Pramod Kumar; Turpu, Goverdhan Reddy; Khilari, Santimoy; Pradhan, Debabrata; Ranganath, Kalluri V.S.
Catalysis Communications, 2016 , vol. 84, p. 89 - 92 Title/Abstract Full Text View citing articles Show Details
2.4. Catalytic reaction
General procedure: 20.0 mg of Mg-NHC was taken into the round bottom flask containing toluene (2.0 mL) and subsequently aldehyde (0.5 mmol) was added.To the resultant mixture nitromethane (2.5 mmol) was added and stirring continued at 60 °C for 12 h. After completion of the reaction, the reaction mixture was filtered to separate the catalyst and purified the product using column chromatography (using Hexane: EtOAc, 9:1). 52%
With diethylzinc; ethanolamine in hexane; toluene
T=0°C; Henry reaction; 48 h;
Klein, Guenter; Pandiaraju, Subramaniam; Reiser, Oliver
Tetrahedron Letters, 2002 , vol. 43, # 42 p. 7503 - 7506 Title/Abstract Full Text View citing articles Show Details
50%
With 1,4,7,10-tetraazacyclododecan in tetrahydrofuran
T=20°C; Henry reaction; 24 h;
Vovard-Le Bray, Chloe; Jiang, Fan; Wu, Xiao-Feng; Sortais, Jean-Baptiste; Darcel, Christophe
Tetrahedron Letters, 2010 , vol. 51, # 34 p. 4555 - 4557 Title/Abstract Full Text View citing articles Show Details
43%
With 2C16H14N2O6(2-)*2Zn(2+)*6H2O in methanol T=20°C; Henry Nitro Aldol Condensation; 24 h;
Martins, Nuno M.R.; Mahmudov, Kamran T.; da Silva, M. Fátima C. Guedes; Martins, Luísa M.D.R.S.; Guseinov, Firudin I.; Pombeiro, Armando J.L.
Catalysis Communications, 2016 , vol. 87, p. 49 - 52 Title/Abstract Full Text View citing articles Show Details
25%
With 2C7H7O3S(1-)*C39H48N6O2(2+); copper(II) acetate monohydrate in methanol T=0°C; Henry reaction; 48 h; enantioselective reaction;
Li, Zhi-Huai; Zhou, Zhi-Ming; Hao, Xiao-Yan; Zhang, Jun; Dong, Xiao; Liu, Ying-Qiang; Sun, Wen-Wen; Cao, Dan
Applied Catalysis A: General, 2012 , vol. 425-426, p. 28 - 34 Title/Abstract Full Text View citing articles Show Details
14%
With [TMG][Lac]
T=20°C; Henry reaction; 20 h;
Jiang, Tao; Gao, Haixiang; Han, Buxing; Zhao, Guoying; Chang, Yanhong; Wu, Weize; Gao, Liang; Yang, Guanying
Tetrahedron Letters, 2004 , vol. 45, # 12 p. 2699 - 2701 Title/Abstract Full Text View citing articles Show Details
10%
With C12H11N7S; manganese(II) acetate in ethanol
T=20°C; Henry reaction;
Zhou, Guang Peng; Hui, Yong Hai; Wan, Ning Ning; Liu, Qiu Ju; Xie, Zheng Feng; De Wang, Ji
Chinese Chemical Letters, 2012 , vol. 23, # 6 p. 690 - 694 Title/Abstract Full Text View citing articles Show Details
With sodium hydroxide
Shinozaki
Yakugaku Zasshi, 1931 , vol. 51, p. 720 Chem.Abstr., 1932 , p. 1269 Full Text View citing articles Show Details
Hoover; Hass
Journal of Organic Chemistry, 1947 , vol. 12, p. 501,504 Full Text View citing articles Show Details
With sodium hydroxide
T=75°C; Einleiten von Kohlendioxyd;
Bourland; Hass
Journal of Organic Chemistry, 1947 , vol. 12, p. 705 Full Text View citing articles Show Details
With magnesium aluminium-ethylate
Villani; Nord
Journal of the American Chemical Society, 1947 , vol. 69, p. 2608 Full Text View citing articles Show Details
With potassium dicarbonate
Kanao
Yakugaku Zasshi, 1927 , # 540 p. 18 Chem. Zentralbl., 1927 , vol. 98, # I p. 2539 Full Text View citing articles Show Details
Nagai; Kanao
Justus Liebigs Annalen der Chemie, 1929 , vol. 470, p. 174 Chem. Zentralbl., 1928 , vol. 99, # II p. 2553 Full Text Show Details
With triethylamine
17 h;
FUJI, Masayuki
Bulletin of the Chemical Society of Japan, 1988 , vol. 61, # 11 p. 4029 - 4036 Title/Abstract Full Text Show Details
With 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran
Ambient temperature;
Ono; Katayama; Nisyiyama; Ogawa
Journal of Heterocyclic Chemistry, 1994 , vol. 31, # 4 p. 707 - 710 Title/Abstract Full Text View citing articles Show Details
With Amberlite IRA-420 (OH-form)
Caldarelli, Marina; Habermann, Joerg; Ley, Steven V.
Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 2 p. 107 - 110 Title/Abstract Full Text View citing articles Show Details
With sodium hydroxide in methanol
T=20°C; Henry reaction; 12 h;
Dumez, Estelle; Faure, Robert; Dulcere, Jean-Pierre
European Journal of Organic Chemistry, 2001 , # 13 p. 2577 - 2588 Title/Abstract Full Text View citing articles Show Details
With hydrotalcite in tetrahydrofuran
T=60°C; Henry reaction; 6.5 h;
Cwik, Agnieszka; Fuchs, Aliz; Hell, Zoltan; Clacens, Jean-Marc
Tetrahedron, 2005 , vol. 61, # 16 p. 4015 - 4021 Title/Abstract Full Text View citing articles Show Details
Crich, David; Ranganathan, Krishnakumar; Huang, Xianhai
Organic Letters, 2001 , vol. 3, # 12 p. 1917 - 1919 Title/Abstract Full Text View citing articles Show Details
With triethylamine
T=20°C; 16 h; Inert atmosphere;
Agut, Juan; Vidal, Andreu; Rodriguez, Santiago; Gonzalez, Florenci V.
Journal of Organic Chemistry, 2013 , vol. 78, # 11 p. 5717 - 5722 Title/Abstract Full Text View citing articles Show Details
With 1H-imidazole in dichloromethane
Henry Nitro Aldol Condensation; 0.166667 h; Hide Experimental Procedure
Rokhum, Lalthazuala; Bez, Ghanashyam
Tetrahedron Letters, 2013 , vol. 54, # 40 p. 5500 - 5504 Title/Abstract Full Text View citing articles Show Details
Typical procedure for solid phase synthesis of nitroalkene:
General procedure: To a solution ofbenzaldehyde (0.106 g, 1 mmol) and nitromethane (0.091 g, 1.5 mmol) inanhydrous dichloromethane (10.0 mL) was added imidazole (0.136 g,2.0 mmol) and stirred for 10 min. To the resulting mixture, polymer-boundtriphenylphosphine (0.5 g, 1.5 mmol) and iodine (0.380 g, 1.5 mmol) wereadded and allowed to stir for additional 50 min. After completion of thereaction, the solution was filtered through a sintered funnel and the resin waswashed successively with dichloromethane (30.0 mL) and saturated aqueoussodium thiosulfate solution (10.0 mL) thrice. The combined dichloromethaneand sodium thiosulfate solution was vigorously shaken in a separating funnelto remove any unreacted iodine. The organic layer was washed with brine(20.0 mL) and separated, dried over anhydrous sodium sulfate, andconcentrated under vacuo. The resultant crude product was purified bycolumn chromatography using 10percent ethyl acetate in hexane to get the pureproduct in 85percent (0.127 g, 0.85 mmol) yield. With 1,4-diaza-bicyclo[2.2.2]octane in acetonitrile
T=0°C; Henry Nitro Aldol Condensation; 24 h; Green chemistry;
2
Ai, Wensi; Shi, Ronghua; Zhu, Liyan; Jiang, Dehong; Ma, Xiaobo; Yuan, Jilan; Wang, Zhouyu
RSC Advances, 2015 , vol. 5, # 31 p. 24044 - 24048 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 39864981 Find similar reactions
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With N,N,N',N'-tetramethylguanidine in diethyl ether
T=0 - 20°C; 6 h; Molecular sieveInert atmosphere;
Yamanaka, Takuto; Kondoh, Azusa; Terada, Masahiro
Journal of the American Chemical Society, 2015 , vol. 137, # 3 p. 1048 - 1051 Title/Abstract Full Text View citing articles Show Details
A
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C
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3
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Rx-ID: 32789952 Find similar reactions
Zhou, Zhi-Ming; Li, Zhi-Huai; Hao, Xiao-Yan; Zhang, Jun; Dong, Xiao; Liu, Ying-Qiang; Sun, Wen-Wen; Cao, Dan; Wang, Jin-Liang
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 10 p. 2113 - 2118 Title/Abstract Full Text View citing articles Show Details
With 2C7H7O3S(1-)*C37H48N6O2(2+); copper (II) acetate monohydrate in methanol T=0°C; Henry reaction; 60 h; stereoselective reaction;
A
B
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4
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Rx-ID: 28166018 Find similar reactions
With aluminum oxide; carbon dioxide
Henry reaction; 18 h; Reactivity; PressureTemperatureSolventReagent/catalyst; chemoselective reaction;
Ballini, Roberto; Noe, Marco; Perosa, Alvise; Selva, Maurizio
Journal of Organic Chemistry, 2008 , vol. 73, # 21 p. 8520 - 8528 Title/Abstract Full Text View citing articles Show Details
5
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Rx-ID: 16467920 Find similar reactions
Multi-step reaction with 2 steps 1: 95 percent / Amberlyst A-27 supported permanganate / CH2Cl2
2: Amberlite IRA-420 (OH-form) View Scheme
Caldarelli, Marina; Habermann, Joerg; Ley, Steven V.
Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 2 p. 107 - 110 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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6
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Rx-ID: 2677945 Find similar reactions
B: 0.52 mg C: 0.13 mg D: 0.011 mg
Mori; Ishiyama; Akita; Suzuki; Mitsuoka; Oishi
Chemical and Pharmaceutical Bulletin, 1990 , vol. 38, # 12 p. 3449 - 3451 Title/Abstract Full Text View citing articles Show Details
With Clostridium innocuum; M10 broth
T=37°C; 120 h;
7
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Hide Experimental Procedure
Rx-ID: 24843128 Find similar reactions
Northwestern University
Patent: US4933505 A1, 1990 ; Title/Abstract Full Text Show Details
7.b:(a)
(b) n-BuLi (1.6 M hexane soln, 3.12 mL) was added dropwise with stirring to a solution of nitropropane (0.45 mL, 5 mmol) in THF (4 mL at -78° C. After 20 minutes the complex (as prepared above) was added and the solution allowed to warm to room temperature. After a further 4 hours the reaction was quenched at 0° C. with an aqueous slurry of disodium EDTA (1.86 g in 10 mL water). The mixture was diluted with water (50 mL) and extracted with Et2 O (3*50 mL). The combined Et2 O extracts were washed with hydrochloric acid (2 M, 50 mL), aqueous sodium bicarbonate (saturated, 50 mL) and water (50 mL, dried and evaporated in vacuo. Flash column chromatography [SiO2 hexane, Et2 O 6:1] gave 1-phenyl-2-nitro-1-propanol (0.271 g, 28percent) Erythro:threo ratio 4.6:1.
8
B
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Rx-ID: 2677943 Find similar reactions
9
A
With N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium in tetrahydrofuran
T=-90°C; varying amount/sequence of addition of reagents; Product distribution;
Yamada, Kazutoshi; Tanaka, Seiji; Kohmoto, Shigeo; Yamamoto, Makoto
Journal of the Chemical Society, Chemical Communications, 1989 , p. 110 - 111 Title/Abstract Full Text View citing articles Show Details
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62%
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Rx-ID: 2042320 Find similar reactions
With hydrogen; sulfided platinum on carbon in hydrogenchloride; ethanol
T=50°C; P=760 Torr; 14 h;
Tamura, Rui; Oda, Daihei; Kurokawa, Hiroshi
Tetrahedron Letters, 1986 , vol. 27, # 47 p. 5759 - 5762 Title/Abstract Full Text View citing articles Show Details
A
B
C
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10
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in water
T=30°C; 48 h; microbial reduction with Rhodococcus rhodochrous IFO 3338; other pH, other microoranism; Product distribution;
Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi
Agricultural and Biological Chemistry, 1985 , vol. 49, # 8 p. 2331 - 2336 Title/Abstract Full Text Show Details
11
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Rx-ID: 7396486 Find similar reactions
With sodium hydroxide
Kamlet
Patent: US2151517 , 1938 ; Full Text Show Details
12
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Rx-ID: 5500470 Find similar reactions
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Kanao
Yakugaku Zasshi, 1927 , # 540 p. 18 Chem. Zentralbl., 1927 , vol. 98, # I p. 2539 Full Text View citing articles Show Details
Nagai; Kanao
Justus Liebigs Annalen der Chemie, 1929 , vol. 470, p. 174 Chem. Zentralbl., 1928 , vol. 99, # II p. 2553 Full Text Show Details