Synthesis of 4⁃Isobutyrate⁃2⁃Cyclohepten⁃1⁃One

doi:10.12422/j.issn.1006-396X.2023.02.010

Journal of Petrochemical Universities ›› 2023, Vol. 36 ›› Issue (2): 78-82.DOI: 10.12422/j.issn.1006-396X.2023.02.010

• Alternative Fuels and New Materials • Previous Articles

Synthesis of 4⁃Isobutyrate⁃2⁃Cyclohepten⁃1⁃One

Tianying Zeng¹(), Jinbo Ma², Fang Yu¹()

^1.School of Petrochemical Engineering，Liaoning Petrochemical University，Fushun Liaoning 113001，China
^2.Shenyang Environmental Monitoring Center，Shenyang Liaoning 110000，China

Received:2021-05-16 Revised:2022-07-11 Published:2023-04-25 Online:2023-05-06
Contact: Fang Yu

4⁃异丁酰氧基⁃2⁃环庚烯⁃1⁃酮的合成研究

曾天映¹(), 马金波², 于芳¹()

^1.辽宁石油化工大学石油化工学院，辽宁抚顺 113001
^2.沈阳市环境监测中心站，辽宁沈阳 110000

通讯作者: 于芳
作者简介:曾天映(1992⁃)，男，硕士研究生，从事过渡金属催化的有机合成研究；E⁃mail：13781914689@163.com。
基金资助:
国家自然科学基金项目(21402078)

Abstract

Abstract:

4?Isobutyloxy?2?cyclohepten?1?one was prepared by the condensation of isobutyryl chloride and 4?hydroxy?2?cyclohepten?1?one.The effects of various amounts of 4?dimethylaminopyridine(DMAP),reaction temperature and reaction time on the esterification reaction were investigated under the condition of no condensation agent.The results show that the optimized reaction condition is 0.3 mmol of DMAP under 25 ℃ for 3 h with a yield of 89%.The results of the NMR show that the synthesized product was the target molecule 4?isobutyloxy?2?cyclohepten?1?one.This esterification reaction features high yields under mild reaction conditions without the involvement of condensation agents,which is in line with the concept of the development of green chemistry.

Key words: Esterification reaction, No condensation agent, Yield

摘要：

通过异丁酰氯和4‐羟基‐2‐环庚烯‐1‐酮缩合制备了4?异丁酰氧基?2?环庚烯?1?酮。在无缩合剂的条件下，考察了4‐二甲氨基吡啶（DMAP）的物质的量、反应温度、反应时间等对酯化反应的影响。结果表明，该反应较佳的DMAP的物质的量为0.3 mmol，较佳温度为25 ℃，较佳的反应时间为3 h；在以上反应条件下，酯化产物的产率为89%。核磁表征结果表明，合成的产物为目标产物4?异丁酰氧基?2?环庚烯?1?酮。该反应条件温和，无需缩合剂参与，产率高，符合绿色化学发展的概念。

关键词: 酯化反应, 无缩合剂, 产率

CLC Number:

TQ215

Tianying Zeng, Jinbo Ma, Fang Yu. Synthesis of 4⁃Isobutyrate⁃2⁃Cyclohepten⁃1⁃One[J]. Journal of Petrochemical Universities, 2023, 36(2): 78-82.

曾天映, 马金波, 于芳. 4⁃异丁酰氧基⁃2⁃环庚烯⁃1⁃酮的合成研究[J]. 石油化工高等学校学报, 2023, 36(2): 78-82.

Figures/Tables 6

Fig.1 Esterification to 4?isobutyrate?2?cyclohepten?1?one

Table 1 Effecting of DMAP catalyst dosage on esterification reaction

n（DMAP）/mmol	产率/%
0	15
0.1	50
0.2	78
0.3	89
0.4	85
0.5	73

Table 2 The effect of temperature on esterification reaction

反应温度/℃	产率/%
-20	31
0	79
10	80
25	89
40	68
60	29

Table 3 The effect of time on esterification reaction

反应时间/h	产率/%
1	40
2	75
3	89
4	89

Fig.2 Speculation mechanism of esterification

Fig.3 1H?NMR and 13C?NMR spectrum of 4?isobutyrate?2?cyclohepten?1?one

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Synthesis of 4⁃Isobutyrate⁃2⁃Cyclohepten⁃1⁃One

4⁃异丁酰氧基⁃2⁃环庚烯⁃1⁃酮的合成研究

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