Formation of dimer-type ketals in the reaction of 2,4,6-trichlorophenol and 2,4,6-trichloro-m-cresol with calcium hypochlorite in methanol:: Conversion to quinones and other compounds

被引：6

作者：

Heasley, VL ^{[1
]}

Anderson, JD ^{[1
]}

Bowman, ZS ^{[1
]}

Hanley, JC ^{[1
]}

Sigmund, GA ^{[1
]}

Van Horn, D ^{[1
]}

Shellhamer, DF ^{[1
]}

机构：

[1] Point Loma Nazarene Univ, Dept Chem, San Diego, CA 92106 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 19期

关键词：

D O I：

10.1021/jo020311n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,4,6-Trichlorophenol (2) and 2,4,6-trichloro-m-cresol (5) react with calcium hypochlorite (Ca(OCl)(2)) in MeOH to give respectively dimer-type ketals 2-(2',4',6'-trichlorophenoxy)-4,4-dimethoxy-6-chlorocyclohexadien-2,5- one (6) and 2-(3'-methyl-2',4',6'-trichlorophenoxy)-4,4-dimethoxy-5-methyl-6-chlorocyclohexadien-2,5-one (7). Ketal 6, which was too unstable to be isolated, and 7 hydrolyzed in H2O/HCl to 2-(2',4',6'-trichlorophenoxy)-6-chloro-1,4-benzoquinone (8) and 2-(3'-methyl-2',4',6'-trichlorophenoxy)-5methyl-6-chloro-1,4-benzoquinone (9), respectively. Ketal 6 and quinone 8 were also produced when 2 and Ca(OCl)(2) reacted in DMF, followed by addition of MeOH and H2O, respectively. The mechanisms of these reactions are examined. Conversion of the ketals and quinones to other products is described.

引用

页码：6827 / 6830

页数：4

共 8 条

[1] Reaction of 2,4,6-trichlorophenol with hypochlorite ion: Examination of products.
Bowman, ZS
Hanley, JC
Sigmund, GA
Heasley, VL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U322 - U322
[2] Sulfate radical-induced degradation of 2,4,6-trichlorophenol: A de novo formation of chlorinated compounds
Xu, Lei
Yuan, Ruixia
Guo, Yaoguang
Xiao, Dongxue
Cao, Yuan
Wang, Zhaohui
Liu, Jianshe
CHEMICAL ENGINEERING JOURNAL, 2013, 217 : 169 - 173
[3] A reinvestigation of the synthesis of Hantzsch's acid: Comparison of derivatives of Hantzsch's acid with a product from the reaction of 2,4,6-trichlorophenol and hypochlorite ion in methanol
Heasley, VL
Wadley, BD
Alexander, MD
Anderson, JD
Anderson, JH
Allen, RT
Hernandez, ML
Ismail, ML
Sigmund, GA
Shellhamer, DF
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23): : 8111 - 8113
[4] Catalytic hydrodechlorination of p-chloro-m-cresol and 2,4,6-trichlorophenol with Pd and Rh supported on Al-pillared clays
Pizarro, A. H.
Monsalvo, V. M.
Molina, C. B.
Mohedano, A. F.
Rodriguez, J. J.
CHEMICAL ENGINEERING JOURNAL, 2015, 273 : 363 - 370
[5] Reactions of 2,4,6-trichlorophenol on model fly ash:: oxidation to CO and CO2, condensation to PCDD/F and conversion into related compounds
Hell, K
Stieglitz, L
Altwicker, ER
Addink, R
Will, R
CHEMOSPHERE, 2001, 42 (5-7) : 697 - 702
[6] Thermolysis of 2,4,6-trichlorophenol chemisorbed on aluminium oxides as example of fly ash mediated surface catalysis reaction in PCDD/PCDF formation
Voncina, E
Solmajer, T
CHEMOSPHERE, 2002, 46 (9-10) : 1279 - 1286
[7] 2,4,6-Trichloro[1,3,5]triazine (TCT)-catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds
Nemati, Firouzeh
Bigdeli, Mohammad A.
Mahdavinia, Gholam Hossein
Kiani, Hossein
GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (02) : 89 - 92
[8] An elementary reaction-kinetic model for the gas-phase formation of 1,3,6,8-and 1,3,7,9-tetrachlorinated dibenzo-p-dioxins from 2,4,6-trichlorophenol
Khachatryan, L
Burcat, A
Dellinger, B
COMBUSTION AND FLAME, 2003, 132 (03) : 406 - 421

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