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ERIC Number: EJ939013
Record Type: Journal
Publication Date: 2011-Jul
Pages: 2
Abstractor: As Provided
Reference Count: 17
ISSN: ISSN-0021-9584
Oxidation of Cyclohexene to "trans"-1,2-Cyclohexanediol Promoted by "p"-Toluenesulfonic Acid without Organic Solvents
Rosatella, Andreia A.; Afonso, Carlos A. M.; Branco, Lus C.
Journal of Chemical Education, v88 n7 p1002-1003 Jul 2011
This experiment describes a method for cyclohexene oxidation to "trans"-1,2-cyclohexanediol using "p"-toluenesulfonic acid ("p"-TsOH) as promoter and hydrogen peroxide as oxidant in a biphasic system. This method allows conversions up to 97.9% (monitored by [superscript 1]H NMR). "trans"-1,2-Cyclohexanediol was not easily separated from the aqueous solution owing to formation of an azeotropic mixture with water. Destruction of the azeotropic mixture was observed in the presence of sodium "p"-toluenesulfonate salt ("p"-TsONa). Therefore, water could be removed by simple distillation after "p"-TsOH neutralization. Purification of "trans"-1,2-cyclohexanediol was accomplished by sublimation. The overall reaction, separation, and purification experiment did not require any organic solvent. (Contains 1 scheme.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A