Synthesis of 1,1-Diacetates Catalyzed by Cellulose Sulfonic Acid from Aldehydes and Acetic Anhydride

Songsong Ding; Jiming Zhang; Wei Shi; Jianhua Zhou

doi:10.14233/ajchem.2015.17926

Issue

Vol. 27 No. 1 (2015): Vol 27 Issue 1

Issue Published : December 27, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of 1,1-Diacetates Catalyzed by Cellulose Sulfonic Acid from Aldehydes and Acetic Anhydride

https://doi.org/10.14233/ajchem.2015.17926

Songsong Ding

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Jiming Zhang

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Wei Shi

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Jianhua Zhou

School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, P.R. China

Corresponding Author(s) : Jiming Zhang

zhangjiming@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 1 (2015): Vol 27 Issue 1
Article Published : December 29, 2014

Abstract

1,1-Diacetates have been synthesized in good to excellent yields via a reaction of corresponding aldehydes and acetic anhydride in the presence of cellulose sulfonic acid as a heterogeneous catalyst at room temperature. The protection of aldehydes generated an anhydro-dimer as single product under similar reaction conditions. The catalysis is equally applicable for the deprotection of acylal in acetonitrile.

Keywords

1 1-Diacetates Cellulose sulfonic acid Reusable catalyst Protection Deprotection

Ding, S., Zhang, J., Shi, W., & Zhou, J. (2014). Synthesis of 1,1-Diacetates Catalyzed by Cellulose Sulfonic Acid from Aldehydes and Acetic Anhydride. Asian Journal of Chemistry, 27(1), 340–342. https://doi.org/10.14233/ajchem.2015.17926

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References

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References

B. Datta and M.A. Pasha, Synth. Commun., 41, 1160 (2011); doi:10.1080/00397911003797866.

R.J. Kalbasi, A.R. Massah and A. Shafiei, J. Mol. Catal. Chem., 335, 51 (2011); doi:10.1016/j.molcata.2010.11.013.

Q. Liu, Fenzi Cuihua, 24, 322 (2010).

F. Shirini, M. Mamaghani and M. Seddighi, Catal. Commun., 36, 31 (2013); doi:10.1016/j.catcom.2013.02.022.

P. Dutta, P. Sarma and R. Borah, Synth. Commun., 43, 1378 (2013); doi:10.1080/00397911.2011.635258.

M. Sandberg and L.K. Sydnes, Org. Lett., 2, 687 (2000); doi:10.1021/ol005535b.

B.M. Trost and C. Lee, J. Am. Chem. Soc., 123, 12191 (2001); doi:10.1021/ja0118338.

E.R. Perez, A.L. Marrero, R. Perez and M.A. Autie, Tetrahedron Lett., 36, 1779 (1995); doi:10.1016/0040-4039(95)00122-S.

T.S. Jin, G.Y. Du and T.S. Li, Indian J. Chem., 37B, 939 (1998).

K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Rajadhyaksha and H.W. Pinnick, J. Org. Chem., 48, 1765 (1983); doi:10.1021/jo00158a036.

B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, M.A. Amrollahi and N. Sheikhan, Russ. J. Org. Chem., 43, 852 (2007); doi:10.1134/S1070428007060085.

Y. Ishino, M. Mihara, T. Takeuchi and M. Takemoto, Tetrahedron Lett., 45, 3503 (2004); doi:10.1016/j.tetlet.2004.02.159.

M.M. Heravi, S. Taheri, K. Bakhtiari and H.A. Oskooie, Monatsh. Chem., 137, 1075 (2006); doi:10.1007/s00706-005-0499-0.

A.R. Hajipour, A. Zarei and A.E. Ruoho, Tetrahedron Lett., 48, 2881 (2007); doi:10.1016/j.tetlet.2007.02.090.

A.K. Bhattacharya, M. Mujahid and A.A. Natu, Synth. Commun., 38, 128 (2007); doi:10.1080/00397910701651284.

M.M. Heravi, K. Bakhtiari, S. Taheri and H.A. Oskooie, Green Chem., 7, 867 (2005); doi:10.1039/b510855c.

A.T. Khan, L.H. Choudhury and S. Ghosh, J. Mol. Catal. Chem., 255, 230 (2006); doi:10.1016/j.molcata.2006.04.008.

H.M.S. Kumar, B.V.S. Reddy, P.T. Reddy and J.S. Yadav, J. Chem. Res (S), 86 (2000); doi:10.3184/030823400103166472.

R. Ghosh, S. Maiti, A. Chakraborty and R. Halder, J. Mol. Catal. Chem., 215, 49 (2004); doi:10.1016/j.molcata.2004.01.018.

H. Firouzabadi, N. Iranpoor and S. Farahi, Scientia Iranica, 15, 413 (2008).

Z.H. Zhang, L. Yin, Y. Li and Y.M. Wang, Tetrahedron Lett., 46, 889 (2005); doi:10.1016/j.tetlet.2004.11.161.

V.T. Kamble, B.P. Bandgar, N.S. Joshi and V.S. Jamode, Synlett, 2719 (2006); doi:10.1055/s-2006-950282.

J.R. Satam and R.V. Jayaram, Catal. Commun., 8, 1414 (2007); doi:10.1016/j.catcom.2006.12.005.

N. Sumida, K. Nishioka and T. Sato, Synlett, 1921 (2001); doi:10.1055/s-2001-18774.

T.S. Jin, G. Sun, Y.W. Li and T.S. Li, Green Chem., 4, 255 (2002); doi:10.1039/b200219a.

A.R. Hajipour, L. Khazdooz and A.E. Ruoho, Catal. Commun., 9, 89 (2008); doi:10.1016/j.catcom.2007.05.003.

N. Deka, D.J. Kalita, R. Borah and J.C. Sarma, J. Org. Chem., 62, 1563 (1997); doi:10.1021/jo961741e.

Issue

Vol. 27 No. 1 (2015): Vol 27 Issue 1

Synthesis of 1,1-Diacetates Catalyzed by Cellulose Sulfonic Acid from Aldehydes and Acetic Anhydride

Corresponding Author(s) : Jiming Zhang

Abstract

Keywords

Full Article

Download Citation

References

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