• Title/Summary/Keyword: Aromatic Aldehydes

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Photoaddition Reactions of Silyl Ketene Acetals with Aromatic Carbonyl Compounds: A New Procedure for β-Hydroxyester Synthesis

  • Yoon, Ung-Chan;Kim, Moon-Jung;Moon, Jae-Joon;Oh, Sun-Wha;Kim, Hyun-Jin;Mariano, Patrick S.
    • Bulletin of the Korean Chemical Society
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    • v.23 no.9
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    • pp.1218-1242
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    • 2002
  • Photochemical reactions of aromatic carbonyl compounds with silyl ketene acetals have been explored. Irradiation of acetonitrile or benzene solutions containing aryl aldehydes or ketones in the presence of silyl ketene acetals is observed to promo te formation of ${\beta}-hydroxyester$, 2,2-dioxyoxetane and 3,3-dioxyoxetane products. The ratios of these photoproducts, which arise by competitive single electron transfer (SET) and classical Paterno-Buchi mechanistic pathways, is found to be dependent on the degree of methyl-substitution on the vinyl moieties of the ketene acetals in a manner which reflects expected alkyl substituent effects on the oxidation potentials of these electron rich donors. An analysis of the product distribution arising by irradiation of a solution containing butyrophenone (6) and the silyl ketene acetal 9, derived from methyl isobutyrate, provides an estimate of the rate constants for the competitive Norrish type Ⅱ, SET and Paterno-Buchi processes occuring. Finally, sequences involving silyl ketene acetal-aryl aldehyde or ketone photoaddition followed by 2,2-dioxyoxetane hydrolysis represent useful procedures for Claisen-condensation type, ${\beta}-hydroxyester$ synthesis.

Studies on Aromatic Dihydrazines (I). Synthesis of p-Phenylenedihydrazine via Tetrazonium Salt and Formation of Dihydrazones (芳香族 디히드라진에 關한 硏究 (第 1 報). 테트라아조늄염을 通한 파라페닐렌디히드라진의 합성 및 디히드라존의 生成)

  • Woo Young Lee
    • Journal of the Korean Chemical Society
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    • v.18 no.1
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    • pp.50-57
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    • 1974
  • A practical method applicable to the synthesis of aromatic dihydrazines was proposed by reducing tetrazonium salt in strong mineral acid media. By diazotizing p-phenylenediamine with sodium nitrite in a medium of concentrated hydrochloric acid or 45 % perchloric acid at $-5 {\sim} -10{\circ}C$ and reducing the tetrazonium salt with stannous chloride, p-phenylenedihydrazine (PPDH) was separated in the form of hydrochloride as colorless fine needles. Since PPDH was subject to oxidation and unstable, the free base could not be isolated. PPDH${\cdot}$2HCl was decomposed at $^180{\circ}C$ without showing sharp melting point. It behaved largely as aromatic monohydrazines, and reacted immediately with aldehydes and ketones in acetate buffer, giving generally yellow to brownish condensation products, dihydrazones. This suggests that PPDH will react with dicarbonyl compounds producing high molecular polymers or cyclization products.

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Constituents of the Essential Oil from Eclipta prostrata L.

  • Chang, Kyung-Mi;Kim, Gun-Hee
    • Preventive Nutrition and Food Science
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    • v.14 no.2
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    • pp.168-171
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    • 2009
  • The volatile aroma constituents of Eclipta prostrata L. (leaves, stems, and flowers) were isolated by hydro-distillation extraction method and analyzed by GC/MS. The yield of Eclipta prostrata L. essential oil was 0.1% (v/w), and its color was yellow. Sixty-eight volatile flavor compounds, which make up 71.15% of the total volatile composition of the essential oil were tentatively characterized. It contained 35 hydrocarbons (56.25%) with sesquiterpene predominating, 12 alcohols (3.05%), 8 ketones (3.83%), 9 aldehydes (1.86%), 2 oxides (6.03%), and 2 esters (0.13%). ${\alpha}$-Humulene, 6,9-heptadecadiene, (E)-${\beta}$-farnesene, and ${\alpha}$-phellandrene were the major abundant aroma components in Eclipta prostrata L., aromatic and medicinal plant.

Zinc (II) [tetra(4-methylphenyl)] Porphyrin: a Novel and Reusable Catalyst for Efficient Synthesis of 2,4,5-trisubstituted Imidazoles Under Ultrasound Irradiation

  • Safari, Javad;Khalili, Shiva Dehghan;Banitaba, Sayed Hossein;Dehghani, Hossein
    • Journal of the Korean Chemical Society
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    • v.55 no.5
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    • pp.787-793
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    • 2011
  • An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or ${\alpha}$-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) [tetra (4-methylphenyl)] porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, ${\alpha}$-hydroxyketones as well as 1,2-diketones were converted to their corresponding 2,4,5-trisubstituted imidazoles in excellent yields.

Synthesis, Characterization and Catalytic Activity of Ce1MgxZr1-xO2 (CMZO) Solid Heterogeneous Catalyst for the Synthesis of 5-Arylidine Barbituric acid Derivatives

  • Rathod, Sandip B.;Gambhire, Anil B.;Arbad, Balasaheb R.;Lande, Machhindra K.
    • Bulletin of the Korean Chemical Society
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    • v.31 no.2
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    • pp.339-343
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    • 2010
  • A series of $Ce_1Mg_xZr_{1-x}O_2$ (CMZO) mixed metal oxide with different molar ratio were prepared by simple co-precipitation method. The prepared materials were tested for their catalytic activity performance using Knoevenagel condensation of various aromatic aldehydes with barbituric acid under solvent-free condition in microwave. The best catalytic activity was obtained with CMZO (1:0.6:0.4). The synthesized materials were characterized by using XRD, FT-IR, SEM-EDS techniques.

Microwave Assisted One-pot Synthesis of Novel α-Aminophosphonates and heir Biological Activity

  • Rao, Alahari Janardhan;Rao, Pasupuleti Visweswara;Rao, Valsani Koteswara;Mohan, Challamchalla;Raju, Chamarthi Naga;Reddy, Cirandur Suresh
    • Bulletin of the Korean Chemical Society
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    • v.31 no.7
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    • pp.1863-1868
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    • 2010
  • A simple and efficient synthesis of various $\alpha$-aminophosphonates (3a-l) by the reaction of substituted aromatic/heterocyclic aldehydes, 2-amino-6-methoxy-benzothiazole and dibutyl/diphenyl phosphites under microwave irradiation without catalyst was accomplished. The phosphonates were characterized by elemental analysis, IR, $^1H$, $^{13}C$- and $^{31}PNMR$ spectra. They showed promising antimicrobial, anti-oxidant activities depending on the nature of bioactive groups at the $\alpha$-carbon.

L-Proline as an Efficient Catalyst for the Synthesis of 2,4,5-Triaryl-1H-Imidazoles

  • Shitole, Nana V.;Shelke, Kiran F.;Sonar, Swapnil S.;Sadaphal, Sandip A.;Shingate, Bapurao B.;Shingare, Murlidhar S.
    • Bulletin of the Korean Chemical Society
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    • v.30 no.9
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    • pp.1963-1966
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    • 2009
  • L-Proline has been found to be an efficient organocatalyst for one-pot synthesis of 2,4,5-triaryl substituted imidazole by the reaction of an aldehyde, a benzil and an ammonium acetate. The short reaction time and excellent yields making this protocol practical and economically attractive.

$TiO_2$-Mediated Photoreactions of Cinnamic Acid and Related Compounds in Methanol

  • Kim, Sung-Sik;Kim, Hyun-Jin;Lee, Hye-Jong;Park, Sang-Kyu
    • Journal of Photoscience
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    • v.10 no.2
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    • pp.181-184
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    • 2003
  • Photochemical reactions of some organic molecules on titanium dioxide were investigated in methanol. A methanolic solution of trans-cinnamic acid and titanium dioxide was irradiated with 300 nm UV lamps for 24 h to afford methyl cinnamate. In the case of trans-cinnamamide, the major product was found to be 3-phenylpropionamide, i.e., a saturation product of ethylenic double bond. However, irradiation of urocanic acid, caffeic acid, ethyl cinnamate, trans-chalcone, trans-cinnamonitrile, trans-stilbene or trans, trans-1,4-diphenyl-1,3-butadiene on titanium dioxide under the same conditions did not give any noticeable products. Meanwhile, when irradiated some aromatic aldehydes, such as trans-cinnamaldehyde, l-naphthaldehyde, and 2-naphthaldehyde in methanol, vicinal diols and alcohols derived from the diols were produced. On the other hand, irradiation of 9-anthraldehyde and titanium dioxide in methanol afforded only alcohols, in which diol was not observed.

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Sensory Characteristics and Volatile Compounds of Cooked Rice according to the Various Cook Method (조리방법에 따른 쌀밥에 관능적 성질 및 휘발성 성분에 관한연구)

  • 송재철
    • The Korean Journal of Food And Nutrition
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    • v.12 no.2
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    • pp.142-149
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    • 1999
  • Moisture absorption rate of rice according to the soaking time was higher at $25^{\circ}C$ than 4$^{\circ}C$ and the op-timum soaking time was 1hr at $25^{\circ}C$. When the ratios of added water for rice cooking were 1.3 in an elec-tric cooker and pressure cooker and 1.7 in an Dookbaeki sensory an mechanically evaluation of cooked rice were highly evaluated. The total number of peak on gas chromatography profile were 89 in an press-ure cooker 56 in an electric cooker and 83 in an Dookbaeki and major volatile compounds of cooked rice were aliphatic hydrocarbons cyclic hydrocarbons aromatic hydrocarbons aldehydes alcohols ketones and thiourea. Furan that is in sweety was not detected in volatile components of cooked rice of electric cooker.

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Analytical Methods for Spatial Distribution of Hazardous Air Pollutants (HAPs)

  • Amagai, Takashi
    • Proceedings of the Korea Air Pollution Research Association Conference
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    • 2010.04a
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    • pp.41-44
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    • 2010
  • Hazardous air pollutants such as benzo[a]pyrene (BaP), benzene, formaldehyde have been concerned about the adverse health effect of long-term exposure. Contour map is useful for finding high-concentration region, emission source, and distributions of HAPs in the ambient air. To make a contour map, we have developed simple analytical method for selected HAPs; polycyclic aromatic hydrocarbons such as BaP, benzene and its derivatives such as toluene and xylene, and aldehydes and ketones. We have applied these methods to investigate air pollution by HAPs in some cities in Japan. The results show that these methods reveal actual emission sources if the PRTR emission report was not submitted.

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