Research on synthesis of m-chloroanisole from 1,3-dichlorobenzene

doi:10.3969/j.issn.1000-2006.2015.05.025

JOURNAL OF NANJING FORESTRY UNIVERSITY ›› 2015, Vol. 39 ›› Issue (05): 150-154.doi: 10.3969/j.issn.1000-2006.2015.05.025

Previous Articles Next Articles

Research on synthesis of m-chloroanisole from 1,3-dichlorobenzene

CAO Mingzhen¹, XU Xu^1,2, BAO Mingkai¹, WANG Shifa^1,2*

1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
2. Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037, China

Online:2015-10-15 Published:2015-10-15

Abstract

Abstract: A new preparation process for m-chloroanisole was explored from 1,3-dichlorobenzene and sodium methoxide. The effects of types of solvent and their dosage, mole ratio of 1,3-dichlorobenzene to sodium methoxide, reaction temperature and reaction time on the conversion rate of 1,3-dichlorobenzene and yield of m-chloroanisole was examined. The optimum synthesis conditions were obtained by orthogonal test as follows: N, N-dimethyl-formamide(DMF)was used as solvent, and solvent dosage was 75 mL/mol; the molar ratio of 1,3-dichlorobenzene to sodium methoxide was 1:1.2; reaction temperature was 120 ℃ and reaction time was 6 h. Under this optimum conditions, the conversion rate of 1,3-dichlorobenzene was 94.8% and the yield of 1,3-chloroanisole was 91.0%. The structure of the m-chloroanisole was analyzed by FT-IR and GC-MS.

CLC Number:

TQ612.1

CAO Mingzhen, XU Xu, BAO Mingkai, WANG Shifa. Research on synthesis of m-chloroanisole from 1,3-dichlorobenzene[J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2015, 39(05): 150-154.

References

[1] Gibson S P,Tommasini I.Preparation of 4-arylpiperidines and their use for treatment of pruritus:JP,2001019672[P]. 2001-01-23.
[2] Flicks K,Frankus E,Fridtrichs E.Phenylsubstituierten aminomethyl cyciohexanolen[J]. Arzneim Forsch, 1978, 28(1): 107-114.
[3] Schlosser M,Heiss C, Marzi E, et al.Protonmobility in 2-substituted 1,3-dichlorobenzenes “ortha ” or “meta” metalation[J]. European Journal of Organic Chemistry, 2006(19): 4398-4404.
[4] Schlotter K,Boecker F, Huebner H,et al. Fancy bioisosteres metallocene-derived g-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles[J]. Journal of Medicinal Chemistry, 2005, 48(11): 3696-3699.
[5] Davis J M,Favor D,Fay L K,et al. Preparation of
[1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia,othermental disorders, and central nervous system disorders:US, 2005043309[P]. 2005-02-24.
[6] Maleczka R E,Shi F,Holmes D,et al.C—H activation/bory lation/oxidation a one-pot unified route to meta-substituted phenols bearing ortho-para-directing groups[J]. Journal of the American Chemical Society, 2003, 125(26):7792-7793.
[7] Zilberman J.One-step preparton of some 3-substituted anisoles[J]. Organic Process Research & Development, 2003(7): 303-305.
[8] Testaferri L,Tiecco M,Tingoli M,et al.The reactions of unactivated aryl halides with sodium methoxide in hmpa[J]. Tetrahedron, 1983, 39(1): 193-197.
[9] Bogdal D,Pielichowski J,Boron A.New synthetic method of aromatic ethers under microwave irradiation in dry medie[J]. Synthetic Communications, 1998, 28(16): 3029-3039.
[10] 薛建荣, 钟宏, 符剑刚. 碳酸二甲酯的用途及合成研究进展[J]. 化工技术与开发,2006, 35(3):8-13. Xue J R,Zhong H,Fu J G.Usage of dimethyl carbonate and its synthesis development[J]. Technology and Development of Chemical Industry, 2006, 35(3): 8-13.
[11] Ouk S,Thiebaud S,Borredon E,et al. O-methylation of phenolic compounds with dimethyl carbonate under solid/liquid phase transfer system[J]. Tetrahedron Letters, 2002, 43(14): 2661-2663.
[12] Langlios B,Soula G.A safe and economical synthesis of 3-(trifluoromethoxy)aniline from 2-chlorophenol [J]. Bulletin de la societe Chimique de France,1986, 6: 925-929.
[13] 董燕敏, 尹振燕, 程琦, 等.碳酸二甲酯作为甲基化试剂合成2,6-二氯苯甲醚[J]. 精细化工,2010, 27(7): 667-671. Dong Y M,Yin Z Y,Cheng Q, et al.Synthesis of 2,6-dichloroanisole with dimethyl carbonate as methylating agent[J]. Fine Chemicals, 2010, 27(7): 667-671.
[14] 陈兴权, 刘洋, 董燕敏, 等. 碳酸二甲酯作甲基化试剂合成邻氯苯甲醚[J]. 精细化工, 2008, 25(8): 817-820. Chen X Q, Liu Y, Dong Y M, et al.Synthesis of O-Chioroanisole with dimethyl carbonate as methylating agent[J]. Fine Chemicals, 2008, 25(8): 817-820.
[15] 与善信, 文瑞明. 相转移催化合成对硝基苯甲醚[J]. 精细化工, 2003, 33(5): 19-20. Yu S X,Wen R M.The synthesis of p-nitroanisole by phase transfer catalysis[J]. Fine Chemicals, 2003, 33(5): 19-20.
[16] 徐晓维, 徐徐, 王石发, 等. 甲基丙烯酸异冰片酯的合成及性能研究[J]. 南京林业大学学报:自然科学版, 2013, 37(4): 133-138. Xu X W, Xu X, Wang S F, et al. Synthesis and properties of isobornyl methacrylate[J]. Journal of Nanjing Forestry University:Natural Sciences Edition, 2013,37(4): 133-138.
[17] National Institute of Standards and Technology. Benzene, 1-chloro-3-methoxy[EB/OL].http://webbook.nist.gov/cgi/cbook.cgi?ID=2845-89-8&Units=SI.

Metrics

Comments

www.nldxb.njfu.edu.cn

Edited ＆ Published by Editorial Department of Nanjing Forestry University(Natural Sciences Edition)
Address： No.159 Longpan Road,Nanjing 210037 Jiangsu,P.R.China
E-mail ：xuebao@njfu.edu.cn , xuebao@njfu.com.cn
Telephone +86-25-85428247,85427076
Distributed by China International Book Trading Corporation P.O. Box 399, Beijing ,P.R. China

Research on synthesis of m-chloroanisole from 1,3-dichlorobenzene

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments

Author

Reader

Reviewer