henry reaction of benzaldehyde

[all data], Benoit, 1973 Timmermans, J., Specific heat of liquids. Wentworth, W.E. [all data], Iskakov and Potapov, 1971 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol, vi- 1-(3,5-dibromophenyl)-2-methyl-2-nitropropan-1-ol C10H11Br2NO3. 1H-NMR spectra, 13C-NMR spectra were recorded on Bruker AM250 NMR spectrometer using CDCl3 as solvent for the samples. 42. Huaxue Tongbao, 1985, 15-16. J. Chem. of all reactions involving this species. Gas-phase proton transfer reactions in xylene-dimethyl ether mixtures, xi- 2-nitro-1-(2-nitrophenyl) propan-1-ol. ; Kirby, S.P., . Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, [all data], Rabalais and Colton, 1973 errors or omissions in the Database. gas phase; Entropy change calculated or estimated; gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; T = 573 - 725K; Reference Sprot(C2H5)2O = 17.0 J/mol K in, gas phase; Entropy change calculated or estimated. Org. Institute of Standards and Technology, nor is it intended to imply Thermodyn., 1975, 7, 1143-1157. Pattern 22-0700, JCPDS) [23] . . such sites. DRB - Donald R. Burgess, Jr. TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director Hunter, E.P. Chem., 1983, 55, 1596. J. The interactive spectrum display requires a browser with JavaScript and J. Chem. Thermodynamic properties of organic oxygen compounds. Previous wok in the synthesis of fine chemicals using layered double hydroxides revealed the importance of such materials and discovered its environmentally favorable routes in comparison to the other catalysts [15] - [20] . The areal rate of the Henry reaction over nanocrystalline MgO at 273 K was 0.015 ± 0.002 μmol m−2 s−1 and was independent of pretreatment temperature over the range of 523–823 K. Addition of (S)-BINOL to nanocrystalline MgO has been reported previously to favor the production of one enantiomer of the Henry reaction. 491,˚C, IR (KBr) υ max/cm−1: 1480 (NO2), 670 (C-Br), 1H NMR (DMSO): δ δ 5.2 (d, 1H, -C=CH), 6.2 (d, 1H, -C=CH), 7.7 - 7.9 (m, 3H, ArH’s), 13C NMR (CDCl3): δ 77.8, 112.33, 123, 128, 131.1, 135.4, 139.5, MS (m/z): 306.5 (M+), Anal. The 99% yield percentage obtained by using clacined Cu:Al 3:1, using M.W at 1.5 - 2 min. rend., 1934, 198, 1394-1395. [all data], Behan, Johnstone, et al., 1976 Ref. J. Indian J. Dry the filtrate at 80˚C in an oven for 16 h. ii- Cu:Mg:Al (1:2:1) HT-2, Clacined Cu:Mg:Al (1:2:1) HT-3, and Clacined Cu:Mg:Al (2:1:1) HT-4. Figure 3: Compare the time change during use of different catalysts, MW irradiation method. For Cu:Al 3:1 and Cu:Mg:Al 2:1:1 the reaction tended to be completed in a short time. [all data], Terenin, 1961 Am. Journal of Molecular Catalysis A: Chemical, https://doi.org/10.1016/j.molcata.2011.03.018. An Academic Publisher, Henry Reaction between Benzaldehyde and Nitromethane over Solid Base Catalysts: A Green Protocol (). Soc., 1977, 99, 3980. Briner, E.; Chastonay, P., The mixture was added in a Teflon vial and irradiated under 350 W microwave till the reaction temperature raised to 120˚C with fixed microwave pressure. on behalf of the United States of America. The authors are very grateful to Taif University, Taif, KSA, because this work was financial supported by Taif University, Taif, KSA, under project number 1/437/4938. View plot The reaction were carried on electrical heating hotplate with stirrer and the methods as mentioned above in microwave irradiated were applied without catalyst at 90˚C and with the catalysts series at 60˚C for the series of catalysts and series of the aldehydes and nitro alkanes. Org. Eng. [all data], Kudchadker and Kudchadker, 1975 Use or mention of technologies or programs in this web site is not Soc., London, 1961, 321. HT series kept their physical properties (texture and structure) even after many catalytic runs, which facilitated gaining of high yields beta nitro alcohols. Comparison between different methods time and yield using clacined Cu:Al (3:1) (0.5 g). Phys., 1957, 26, 542. Watanabe, K.; Nakayama, T.; Mottl, J., form is Kudchadker S.A., Stephenson, Richard M.; Malanowski, Stanislaw, until the reaction reached the end. 453.3˚C, IR (KBr) υ max/cm−1: 3650 (OH), 1520 - 1570 (2NO2), 1H NMR (DMSO): δ 1.04 (s, 3H, CH3), δ 5.15 (s, H, CH), δ 6.7 - 7.2 (m, 4H, ArH’s), 13C NMR (CDCl3): δ 25.12, 39.9, 77.82, 88.65, 112.86, 116.75, 129.36, 150.99, MS (m/z): 240.12 (M+), Anal. Ber. ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. Thermochemistry and kinetic energy release, The catalyst was also analyzed after reuse by XRD and it showed no significant change. [all data], Ramart-Lucas and Guilmart, 1950 [all data], Anselme and Teja, 1990 The greatest challenge in the selective synthesis of 2-nitroalkanols in the multiple product options such as aldol olefin and its polymer and Cannizaro products is the selection of the right type of base [7] . Chem., 1975, 79, 1161. All of carbonate bands of HT catalysts were removed completely during calcinations at 450˚C [26] . Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Keep the temperature at 60˚C overnight (16 h) in water bath. and HTML 5 enabled browser. . In the last decade, there were notable improvements in the development of heterogeneous catalyst for Henry reaction [10] . . Catalysts 0.5 g from HT-1 up to HT-5 were used and added by repeated adequate sequence to a reaction mixture as mentioned above for the series a - o till the reaction completed as before. ; Bentley, T.W., Chem. Benzaldehyde and furfural (2-furaldehyde), Obshchei Khim., 1934, 4, 1027-1033. Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 Keep the temperature at 60˚C overnight (16 h) in water bath. It is similar to the Aldol Addition, and also referred to as the Nitro Aldol Reaction. CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. The benzoyl ion. National Institute of Standards and H2O, mix (C), mixing of 0.7162 mol of NaOH, and 0.2084 mol of Na2CO3, in a dist. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below. Thermodynamic properties in the gaseous state of certain monosubstituted benzenes, 2) Synthesis of β-Nitroalcohol, via Henry Reaction. ; Chen, E., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Nanocrystalline MgO catalysts for the Henry reaction of benzaldehyde and nitromethane. Molecular and Atomic Volumes. Copyright © 2011 Elsevier B.V. All rights reserved. Landrieu, P.; Baylocq, F.; Johnson, J.R., Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 xv- 1-(4-methoxyphenyl)-2-methyl-2-nitropropan-1-ol. ; Kebarle, P., De Maré, G.R. High Energy Chem., 1971, 5, 238, In original 265. ; Hales, J.L. The vapour pressure of benzaldehyde between 273 and 376 K, The authors presented the abstract as poster at Green and sustainable chemistry conference 13-15 May 2017, Berlin. Proc. Then Cu-modified Mg-Al catalysts were prepared in oven at 500˚C for 7 h under a flowing stream of pure N2. ix- 4-bromo-2-(1-hydroxy-2-methyl-2-nitropropyl)-6-nitrophenol. Thermodynamic properties of organic oxygen compounds 42. The critical properties of rapidly reacting substances, Faraday Trans., 1958, 54, 949. xiv- 1-(4-methoxyphenyl)-2-nitropropan-1-ol. mp. Physical and thermodynamic properties of benzaldehyde, ; Freiser, B.S., Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 ; Turner, D.W., vii- 1-(3,5-Dibromophenyl)-2-nitro-1-propene (C9H7Br2NO2). It was prepared also by coprecipitation methods as mentioned in literature, where mixing of magnesium nitrate Cu SO4・5H2O 0.028 mol, and aluminium nitrate Al (NO3)3 0.01 mol, in a dist. Drop using a burette drops from Mix (C) and Mix (D) to a round bottle flask 1L containing 0.5 L distilled water under vigorous stirring and heating at 60˚C and measure pH during precipitation to be 10-11. © 2018 by the U.S. Secretary of Commerce 440.3˚C, IR (KBr) υ max/cm−1: 3550 (OH), 1523-1550 (NO2), 670 (C-Br), 1H NMR (DMSO): δ 3.15 (d, 2H, CH2), δ 7.27 - 7.4 (dd, 4H, ArH’s), δ 5.2 (t, 1H, -CH), 13C NMR (CDCl3): δ 25.5, 39.8, 77.8, 88.7, 124.4, 129.8, 131.1, 135.1 , MS (m/z): 353.3 (M+), Anal. Part VII. Small weak band appeared at 1650-1700. [all data], Buckingham and Donaghy, 1982 by using conventional method in a max. Table 1 represents the nitroalkanes and the aldehydes used. Part 5. J. Farid, R.; McMahon, T.B., Chem. Kolosovskii, N.A. Calculation and qualitative predictions of mass spectra. Copyright © 2020 Elsevier B.V. or its licensors or contributors. Figure 5. spectrum (can be printed in landscape orientation). 552˚C, IR (KBr) υ max/cm−1: 1515 - 1560 (2NO2), 1H NMR (DMSO): δ 1.04, (d, 3H, CH3), δ 3.45 (m, H, CH), δ 5.15 (d, H, CH), δ 6.7 - 7.3 (m, 4H, ArH’s), 13C NMR (CDCl3): δ 18.1, 44.73, 77.8, 84.74, 112.87, 116.75, 129.3, 150.9, MS (m/z): 226 (M+), Anal. Bull. Behan, J.M. 362˚C, IR (KBr) υ max/cm−1: 3600 (OH), 1520 - 1580 (2NO2), 675 (C-Br), 1H NMR (DMSO): ): δ 1.75(d, 3H, CH3) , 4.95 (m, H, C=CH), δ 7.7 - 7.9 (m, 3H, ArH’s), 13C NMR (CDCl3): δ 24.9, 77.8, 119.83, 123, 128, 130, 131.5, 139.5, MS (m/z): 320.91 (M+), Anal. One also could observe that aldehyde which has little electron withdrawing group influence and enhance the reaction activity. Ambrose D., and chemical property data is available from the ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein Table 2. Enter the desired X axis range Filter using (Whatmann 1 filter paper) and washing the cake by hot distilled water till pH = 7 gives (HT-5). mp. Electron affinities of substituted aromatic compounds, [all data], Rao, 1975 Calcd for C9H9Br2NO3 (339), Br-47.2; C-31.85; H-2.65; N-6.85% Found: Br-47.14; C-31.89; H-2.68; N-4.13; %. ; Traeger, J.C., The reactants aldehydes, nitroalkanes and catalyst were added together in a round flask bottle, closed with rubber septum connected to a condenser, after the completion of the reaction, the mixture cooled room air temperature then separated and purified as above mentioned and also the catalyst was treated as the above method. Mass Spectrom., 1979, 14, 434. HL - Edward P. Hunter and Sharon G. Lias AC - William E. Acree, Jr., James S. Chickos H2O, mix (A). Catalysts were prepared by co-precipitation methods as literature [29] [30] , LDHs have the structures [, (OH)2]x+ [Ax/y]y−. [all data], McLoughlin and Traeger, 1979 Individual Reactions By formula: Br - + C 7 H 6 O = ( Br - • C 7 H 6 O ) ; Cooks, R.G., Significant improvements to the Henry reaction have been achieved by using silyl nitronates in the presence of fluoride ion or altematively α-α doubly deprotonated primary nitroalkanes [8] . ► Nano-MgO is an effective catalyst for reaction of benzaldehyde and nitromethane. Cox, J.D. 465˚C, IR (KBr) υ max/cm−1: 1530 (NO2), 1H NMR (DMSO): δ 1.1 (s, 3H, CH3), δ 5.1 (s, H, CH), δ 7.27 - 7.4 (dd, 4H, ArH’s), 13C NMR (CDCl3): δ 25.5, 39.5, 77.82, 81.1 126.66, 130.8, 134.5, MS (m/z): 230.01 (M+), Anal. Freezing points of some organic fluids, The solid base catalysts provide an alternative to the classical soluble bases with emphasize to avoid the environmental problems caused by salt formation and hazardous conditions [14] . 1.) To generalize this reaction methodology three experiments were carried out using different LDHs catalysts which may also be called hydrotalcite, and their thermally activated form (calcined) were very active and very useful in many different organic synthesis reactions. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985