Transition Metal Catalyzed the Double Hydrohydroxymethylation of Carbonyl Compounds by a Carbon Monoxide-Water System 


Vol. 30,  No. 1, pp. 101-104, Feb.  1986


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  Abstract

아디파알데히드, 구르타르알데히드 및 숙신알데히드와 같은 디알데히드는 물-에톡시에탄올 및 에탄올내에 촉매량의 육로듐 십육카르보닐 또는 오카르보닐철의 존재하, 70기압, 일산화탄소, 180℃, 4시간동안 반응시켜 쉽게 환원되어 대응하는 1,6-헥산디올 및 1,5-펜탄디올 및 1,4-부탄디올이 좋은 수득율로 얻어졌다. 같은 조건하에서 2,5-헥산디온, 2,4-펜탄디온도 대응하는 디올이 보통 수득율로 얻어졌다. 디알데히드의 이중 히드로히드록시메틸화 반응에 대해서는 금속카르보닐 촉매가 다른 촉매보다 더욱 활성적이다. 특히 벤조퀴논은 정량적으로 히드로퀴논을 주었다. Dialdehydes such as adipaldehyde, glutaraldehyde, and succinaldehyde were readily reduced to give their corresponding 1,6-hexanediol, 1,5-pentanediol, and 1,4-butanediol in good yields in the presence of catalytic amount of hexarhodium hexadecacarbonyl or iron pentacarbonyl in water and methoxyethanol or ethanol at 180℃ for 4 hr under carbon monoxide atmosphere. Under the same reaction conditions, diketones such as 2,5-hexanedione, 2,4-pentanedione, and 2,3-butanedione afforded their corresponding 2,5-hexanediol, 2,4-pentanediol and 2,3-butanediol in moderate yields. For double hydrohydroxymethylation of dialdehydes or diketones, rhodium or iron carbonyl complexes are more effective than others. Particularly, benzoquinone gave hydroquinone quantitatively.

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  Cite this article

[IEEE Style]

S. C. Shim, K. E. Mien, K. T. Huh, "Transition Metal Catalyzed the Double Hydrohydroxymethylation of Carbonyl Compounds by a Carbon Monoxide-Water System," Journal of the Korean Chemical Society, vol. 30, no. 1, pp. 101-104, 1986. DOI: .

[ACM Style]

Sang Chul Shim, Kyung Eun Mien, and Keun Tae Huh. 1986. Transition Metal Catalyzed the Double Hydrohydroxymethylation of Carbonyl Compounds by a Carbon Monoxide-Water System. Journal of the Korean Chemical Society, 30, 1, (1986), 101-104. DOI: .

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ISSN(Print) 1017-2548
ISSN(Online) 2234-8530