• Title/Summary/Keyword: benzylic alcohol

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Catalytic Hydrogenation of Aromatic Nitro Compounds over Borohydride Exchange Resin Supported Pd (BER-Pd) Catalyst

  • Yoon, Nung-Min;Lee, Hyang-Won;Choi, Jae-Sung;Lee, Hyun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.14 no.2
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    • pp.281-283
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    • 1993
  • Aromatic nitro compounds are selectively hydrogenated to the corresponding amines in high yields at room temperature and atmospheric pressure using BER-Pd catalyst without affecting ketone, ether, ester, nitrile or chloro groups also present. Especially the nitro group in 4-nitrobenzyl alcohol, methyl 4-nitrobenzyl ether and N-N-dimethyl 4-nitrobenzylamine is selectively hydrogenated with this catalyst to give the corresponding amines without hydrogenolysis of benzylic groups. And aromatic nitro compound can be reduced selectively in the presence of aliphatic nitro compound.

Carbonylation of 1-Bromo-2,6-bis(bromomethyl)benzene Catalyzed by Cobalt Carbonyl

  • Sang Chul Shim;Shin Ae Chae;Dong Yeob Lee;Young Zoo Youn;Jae Goo Shim;Chil Hoon Doh
    • Bulletin of the Korean Chemical Society
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    • v.14 no.4
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    • pp.481-485
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    • 1993
  • Dialkyl 1-bromobenzene-2,6-diacetates were easily prepared by the carbonylation of the moiety of benzylic bromide in 1-bromo-2,6-bis(bromomethyl)benzene with alcohol in the presence of NaOAc< TEX>${\cdot}$3H$_2$O and a catalytic amount of Co$_2$(CO)$_8$under the atmospheric pressure of carbon monoxide at room temperature in excellent yield. Alkyl 2,6-bis(alkoxymethyl)benzoates were obtained by the carbonylation of the moiety of aryl bromide in 1-bromo-2,6-bis(alkoxymethyl)-benzene, which derived from 1-bromo-2,6-bis(bromomethyl)benzene, alcohol, NaOR, and CH$_3$I under the same conditions. Alkyl 2,6-bis(carboxymethyl)benzoate was also obtained in a trace amount for 24 hrs at room temperature.

Cobalt Carbonyl Catalyzed Selective Mono-Carbonylation of Halobenzyl Halide (Ⅰ) (코발트 카르보닐을 촉매로한 할로겐화할로벤질의 선택적 모노-카르보닐화 (Ⅰ))

  • Sim, Sang Cheol;Do, Chil Hun;Yun, Yeong Ju;Jo, Chan Sik;U, Byeong Won
    • Journal of the Korean Chemical Society
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    • v.34 no.6
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    • pp.658-662
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    • 1990
  • A method for regioselective mono-carbonylation of halobenzyl halide is described. Alkyl halophenylacetate is easily prepared by carbonylating a benzylic halide of halobenzyl halide in the presence of catalytic amount of cobalt carbonyl, a base, and an alcohol under atmospheric pressure of carbon monoxide. The base plays a decisive role in the selectivity of product and NEt$_3$ is the best one among bases used.

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A Total Synthesis of Nuciferal and Nuciferol

  • Lee, Woo-Young;Lee, Youn-Young;Lim, Kwang-Su;Goo, Yang-Mo;Park, Oee-Sook
    • Bulletin of the Korean Chemical Society
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    • v.9 no.6
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    • pp.379-381
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    • 1988
  • Racemic nuciferal(1) and nuciferol(2), the terpenic natural perfumeries, have been synthesized by a simple procedure. The benzylic halide 6; 1-(1-chloroethyl)-4-methylbenzene, was prepared by converting p-tolualdehyde(4) into 1-(p-tolyl)-1-ethanol(5), followed by convertion of 5 into corresponding chloride. The Grignard reagent of 6 was reacted with the bromoacetal 7, 2-(2-bromoethyl)-1,3-dioxolane, to give a crosscoupling product 8, which was hydrolysed to 4-(p-tolyl)-pentanal (9). The Wittig reaction of isopropylide 10 with 9 yielded arcurcumen(11). The stereospecific allylic oxidation of the gem-dimethyl olefin 11 with selenium dioxide afforded a trans-aldehyde, (${\pm}$)-1, which was reduced to corresponding alcohol, (${\pm}$)-2.

Facile Synthesis of Dendritic Benzyl Chlorides from Their Alcohols with Methanesulfonyl Chloride/$Et_3N$ (덴드리틱 벤질 클로라이드의 효율적인 합성)

  • Lee, Jae-Wook;Han, Seung-Choul;Kim, Hee-Joo;Kim, Jung-Hwan;Lee, Un-Yup;Kim, Byoung-Ki;Sung, Sae-Reum;Kang, Hwa-Shin;Kim, Ji-Hyeon;Huh, Do-Sung
    • Polymer(Korea)
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    • v.31 no.5
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    • pp.417-421
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    • 2007
  • A successful rapid synthesis of dendritic benzyl chlorides from dendritic benzyl alcohols using methanesulfonyl chloride/$Et_3N$ as activating agents was described. In this method, each dendritic benzyl chloride can be prepared in one pot: no isolation of intermediate mesylated dendrons is required. The key steps in the syntheses of dendritic benzyl chlorides were the mesylation of the hydroxymethyl group followed by the chlorination by in-situ generated triethylammonium chloride.