Oxidative coupling of 4-substituted 2-methoxy phenols using methyltributylammonium permanganate in dichloromethane

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 943-946

  Marques, Francisco A ^a   Simonelli, Fabio ^a   Oliveira, Alfredo R M ^a   Gohr, George L ^a   Leal, Paulo C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

DICHLOROMETHANE; DIMER; GUAIACOL; OXIDIZING AGENT; PHENOL DERIVATIVE; QUINONE DERIVATIVE;

ANION TRANSPORT; AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; METHODOLOGY; OXIDATION; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 0032567892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10665-7     Document Type: Article

References (13)

1. 1. McDonald, P. D.; Hamilton, G. A. In Oxidation in Organic Chemistry ; Trahanovski, W. S. Ed.; Academic Press, New York, 1973, Part B, pp 97.
2. 2. Taylor, W. I.; Battersby, A. R. In Oxidative Coupling of Phenols; Dekker, New York, 1967.
3. 3. Wijnberg, H. Bioorg. Chem. 1978, 7, 397.
4. 4. Kametani, T.; Fukumoto, K. Synthesis 1972, 657.
5. 5. Musso, H., Angew. Chem. 1963, 75, 965.
6. 6. MacRae, W. D.; Towers, G. N. N. Phytochemistry 1984, 23, 1207.
7. 7. Bock, H. and Jaculi, D. Angew. Chem. Int. Ed. Engl. 1984, 23, 305.
8. 4, filtered and the solvent was removed under reduced pressure. The product obtained was purified by a quick filtration through a short pad of silica using a mixture of hexane/ethyl acetate (3:1 ratio) followed by a flash chromatograpy on silica gel with the same mixture of solvents, yielding 254 mg (52%) of dimer 6.
9. 4. After filtration, the dichloromethane was removed under reduced pressure and the product, a dark purple solid, was kept under high vacuum for one hour affording 1.277 g (90%) of the oxidant salt.
10. +, 100), 283, 69, 57.
11. 4: C, 73.64; H, 6.74. Found: C, 73.54; H, 6.85.
12. 4: C, 72.75; H, 7.87. Found: C, 72.77; H, 8.12.
13. 4: C, 70.06; H, 6.61. Found: C, 70.30; H, 6.60.