Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter December 30, 2014

Practical synthesis of 2,3-dimethoxy-5-hydroxymethyl-6-methyl-1,4-benzoquinone

  • Jin Wang EMAIL logo , Shuo Li , Tao Yang , Jin-Rong Zeng and Jian Yang
From the journal Chemical Papers

Abstract

2,3-dimethoxy-5-hydroxymethyl-6-methyl-1,4-benzoquinone (V) was prepared with a 75 % yield by means of a reaction sequence starting from 2,3,4,5-tetramethoxytoluene via Blanc chloromethylation reaction, Kornblum oxidation, NaBH4 reduction and ceric ammonium nitrate oxidation. The procedure is operationally simple and amenable to gram-scale synthesis.

References

Astolfi, P., Charles, L., Gigmes, D., Greci, L., Rizzoli, C., Sorana, F., & Stipa, P. (2013). Reactions of nitric oxide and nitrogen dioxide with coenzyme Q: involvement of the isoprenic chain. Organic & Biomolecular Chemistry, 11, 1399-1406. DOI: 10.1039/c2ob27198b.10.1039/c2ob27198bSearch in Google Scholar PubMed

Bentinger, M., Brismar, K., & Dallner, G. (2007). The antioxidant role of coenzyme Q. Mitochondrion, 7, S41-S50. DOI: 10.1016/j.mito.2007.02.006.10.1016/j.mito.2007.02.006Search in Google Scholar PubMed

Freeman, F., Ribagorda, M., & Adrio, J. (2007). e-EROS Encyclopedia of reagents for organic synthesis. Hoboken, NJ, USA: Wiley. DOI: 10.1002/047084289x.10.1002/047084289XSearch in Google Scholar

Jung, Y. S., Joe, B. Y., Cho, S. J., & Konishi, Y. (2005). 2,3- Dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4- naphthoquinones: glycation inhibitors with lipid peroxidation activity. Bioorganic & Medicinal Chemistry Letters, 15, 1125-1129. DOI: 10.1016/j.bmcl.2004.12.029.10.1016/j.bmcl.2004.12.029Search in Google Scholar PubMed

Lipshutz, B. H., Lower, A., Berl, V., Schein, K., & Wetterich, F. (2005). An improved synthesis of the “miracle nutrient” coenzyme Q10. Organic Letters, 7, 4095-4097. DOI: 10.1021/ol051329y.10.1021/ol051329ySearch in Google Scholar PubMed

Ma, W., Li, D. W., Sutherland, T. C., Li, Y., Long, Y. T., & Chen, H. Y. (2011). Reversible redox of NADH and NAD+ at a hybrid lipid bilayer membrane using ubiquinone. Journal of the American Chemistry Society, 133, 12366-12369. DOI: 10.1021/ja204014s.10.1021/ja204014sSearch in Google Scholar PubMed

Nyland, R. L., Luo, M. H., Kelley, M. R., & Borch, R. F. (2010). Design and synthesis of novel quinone inhibitors targeted to the redox function of apurinic/apyrimidinic endonuclease 1/redox enhancing factor-1 (Ape1/Ref-1). Journal of Medicinal Chemistry, 53, 1200-1210. DOI: 10.1021/jm9014857.10.1021/jm9014857Search in Google Scholar PubMed PubMed Central

Okamoto, K., Matsumoto, M., Watanabe, M., Kawada, M., Imamoto, T., & Imada, I. (1985). Effects of 6-(ω-substituted alkyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinones and related compounds on mitochondrial succinate and reduced nicotinamide adenine dinucleotide oxidase systems. Chemical and Pharmaceutical Bulletin, 33, 3745-3755.10.1248/cpb.33.3745Search in Google Scholar PubMed

Okamoto, K., Watanabe, M., Morimoto, H., & Imada, I. (1988). Synthesis, metabolism, and in vitro biological activities of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4- benzoquinone (CV-2619)-related compounds. Chemical and Pharmaceutical Bulletin, 36, 178-189.10.1248/cpb.36.178Search in Google Scholar PubMed

Tsoukala, A., & Bjørsvik, H. R. (2011). Synthetic route discovery and introductory optimization of a novel process to idebenone. Organic Process Research & Development, 15, 673-680. DOI: 10.1021/op200051v.10.1021/op200051vSearch in Google Scholar

Wang, J., Yang, J., Yang, B., Hu, X., Sun, J. Q., & Yang, T. (2010a). A green and efficient synthesis of 1-chloromethyl-2,3,4,5-tetramethoxy-6-methylbenzene. Journal of Chemical Research, 34, 717-718. DOI: 10.3184/030823410x12857507693437.10.3184/030823410X12857507693437Search in Google Scholar

Wang, J., Yang, J., Yang, B., Sun, J. Q., & Yang, T. (2010b). Alternative synthesis of 5-chloromethyl-2,3-dimethoxy-6-methyl-1,4-benzoquinone: a key intermediate for preparing coenzyme Q analogues. Journal of Chemical Research, 34, 724-725. DOI: 10.3184/030823410x12857507693464.10.3184/030823410X12857507693464Search in Google Scholar

Wang, J., Yang, J., Zhou, R. G., Yang, B., & Wu, Y. S. (2011a). Alternative synthesis of 2-(4-benzoyl-piperazin-1- ylmethyl)-5,6-dimethoxy-3-methyl-[1,4] benzoquinone. Journal of Chemical Research, 35, 431-432. DOI: 10.3184/17475 1911x13099411630089.Search in Google Scholar

Wang, J., Yang, J., Zhou, R. G., Yang, B., & Wu, Y. S. (2011b). A facile synthesis of 2,3-dimethoxy-5-methyl-1,4- benzoquinones. Journal of Chemical Research, 35, 428-430. DOI: 10.3184/174751911x13099377293263.10.3184/174751911X13099377293263Search in Google Scholar

Wang, J., Zhou, R. G., Wu, T., Yang, T., Qin, Q. X., Li, L., Yang, B., & Yang, J. (2012). Total synthesis of apigenin. Journal of Chemical Research, 36, 121-122. DOI: 10.3184/174751912x13285269293913.10.3184/174751912X13285269293913Search in Google Scholar

Xu, G., Wu, J. P., Ai, X. M., & Yang, L. R. (2007). Microwaveassisted Kornblum oxidation of organic halides. Chinese Chemical Letters, 18, 643-646. DOI: 10.1016/j.cclet.2007.04.003. 10.1016/j.cclet.2007.04.003Search in Google Scholar

Received: 2014-5-8
Revised: 2014-7-6
Accepted: 2014-7-10
Published Online: 2014-12-30
Published in Print: 2015-3-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

Downloaded on 31.5.2024 from https://www.degruyter.com/document/doi/10.1515/chempap-2015-0001/html
Scroll to top button