Effect of Layered Double Hydroxide for Alkylation of Carboxylic Acid and Phenol with Alkyl Halide

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  • SHIMADA Hiroshi
    Department of Chemistry, School of Science, Tokai University; 1117 Kitakaname, Hiratsuka-shi 259-1292 Japan
  • HAMAOKA Masaru
    Department of Chemistry, School of Science, Tokai University; 1117 Kitakaname, Hiratsuka-shi 259-1292 Japan

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  • カルボン酸およびフェノールのアルキル化反応における層状複水酸化物の反応速度促進効果
  • カルボンサン オヨビ フェノール ノ アルキルカ ハンノウ ニ オケル ソウジョウフクスイサンカブツ ノ ハンノウ ソクド ソクシン コウカ

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Abstract

The effect of layered double hydroxide (LDH) for alkylation of carboxylic acid or phenol with alkyl halide in toluene was examined. Among a series of LDHs, [Mg2+1-xAlx3+(OH)2][An-x/nyH2O](An-=CO32-, OH- and NO3-), the LDHs containing the strong base anions such as CO32- or OH- group was found to be effective. The desired alkylated products could be obtained in high yield (>70%) from both benzoic acid and phenol in the presence of LDH containing CO32-.<BR>The interaction between the LDH and benzoic acid was examined by using XRD and infrared (IR) techniques. The basal spacing of LDH containing CO32- and OH- increased after the action of toluene solution containing benzoic acid, whereas no expansion of basal spacing was observed in the case of LDH containing Cl-. FT-IR spectrum of the benzoic acid-containing LDH showed the presence of carboxylate ion. These implied that the protonic organic compounds on LDH containing the strong base anions are intercalated as organic anions its interstitial and thus alkylation are accelerated.

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