Paper
Synthesis of 1,4-Dioxaspira[4.5]decan-8-one
Published 2006 · Zhang Feng-bao
Journal of Chemical Engineering of Chinese Universities
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Abstract
1,4-Dioxaspiro[4.5]decan-8-one is an exceedingly useful bifunctional synthetic intermediate and has been widely used in synthesizing organic chemicals, such as pharmaceutical intermediates, liquid crystals and insecticides. Taken 1,4,9,12-tetraoxadispiro[4.2.4.2] tetradecane as raw material, 1,4-Dioxaspiro[4.5]decan-8-one was synthesized via selective deketalization in acidic solution, and the products were characterized by IR and 1HNMR. After comparing the catalytic effects of different acids, the acetic acid (HAc) was selected as the catalyst. The possible mechanism of selectivity and its influence factors were discussed and the optimization of the operation conditions was also conducted. The results show that, comparing with the preparing method proposed by literature, under the optimum reaction conditions (i.e. reaction temperature=65℃, volume ratio HAc/H2O=5:1 and reactant concentration=0.05g?mL?1), the chromatographic yield of 1,4-Dioxaspiro[4.5]decan-8-one is raised to 80% from 65% and the reaction time is reduced to 11 min from 15 h.
Under optimal reaction conditions, 1,4-Dioxaspiro[4.5]decan-8-one synthesis can be achieved with 80% chromatographic yield and 11 minutes reaction time, improving the synthetic process for pharmaceutical intermediates and liquid crystals.
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