合成1,2-环十二二酮的新方法

应用化学, 2009, 26(11): 1374-1376. doi: 10.3969/j.issn.1000-0518.2009.11.028

合成1,2-环十二二酮的新方法

陈韶蕊 ^1, , 马吉海 ^2, , 周雪琴 ^3, , 刘东志 ^4,

1.天津大学化工学院,天津,300072;河北科技大学理学院,石家庄

2.河北科技大学理学院,石家庄

3.天津大学化工学院,天津,300072

4.天津大学化工学院,天津,300072

基金项目: 河北省自然科学基金(B200400278)

关键词：十二烷二酸 , 偶联缩合 , 环十二二酮

A Novel Synthetic Method of 1,2-Cyclododecandione

Keywords： dodecanedioic acid , acyloin condensation , cyclododecandione

以十二烷二酸(1)为原料,与甲醇酯化生成十二烷二酸二甲酯(2),收率为86.5%.化合物2经偶联缩合得1,2-二三甲基硅氧基环十二烯(3),收率为63.1%. 利用溴氧化化合物3得到1,2-环十二二酮(4)淡黄色晶体,收率79%,全过程收率达43.1%,是合成1,2-二酮的新方法. 目标化合物结构经红外光谱、核磁共振氢谱和碳谱表征确认.

1,2-Cyclododecandione (4) was synthesized from dodecanedioic acid via esterification, acyloin condensation, oxidation in an overall yield of 43. 1 %. Reaction of dodecanedioic acid with methanol gave dodecanedioic acid dimethyl ester(2) with a yield of 86. 5%. Compound 3 was obtained from compound 2 through acyloin condensation and the yield reached up to 63. 1% , which was oxidized to compound 4 by bromine water as the oxidation reagent with a yield of 79%. The target compound was a light yellow crystal and was characterized by means of IR, ~1H NMR and ~(I3)C NMR.

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