(b) T. Miyazawa, T. Endo, S. Shiihashi and M. Ogawara, J. Org.
Chem., 1985, 50, 1332; (c) J. M. Bobbitt and M. C. L. Flores,
Heterocycles, 1998, 27, 509; (d) Z. Ma and J. M. Bobbitt, J. Org.
Chem., 1991, 56, 6110; (e) J. M. Bobbitt, J. Org. Chem., 1998, 63,
9367; (f) C. A. Kernag, J. M. Bobbitt and D. V. McGrath,
Tetrahedron Lett., 1999, 40, 1635; (g) N. Merbouh, J. M. Bobbitt
Notes and references
1 (a) M. F. Schlecht, in Comprehensive Organic Synthesis, eds.
B. M. Trost, I. Fleming and S. V. Ley, Pergamon, Oxford, 1991,
vol. 7, pp. 251–327; (b) Modern Oxidation Methods, ed. J.-E.
Backvall, Wiley-VCH, Weinheim, Germany, 2004.
¨
2 (a) R. W. Drugger, J. A. Ragan and D. H. Brown Ripin, Org.
Process Res. Dev., 2005, 9, 253; (b) J. S. Carey, D. Laffan,
C. Thomson and M. T. Williams, Org. Biomol. Chem., 2006, 4,
2337; (c) S. Caron, R. W. Dugger, S. G. Ruggeri, J. A. Ragan and
D. H. Brown Ripin, Chem. Rev., 2006, 106, 2943.
and C. Bruckner, J. Org. Chem., 2004, 69, 5116; (h) J. M. Bobbitt
¨
and N. Merbouh, Org. Synth., 2005, 82, 80; (i) M. Shibuya,
M. Tomizawa and Y. Iwabuchi, J. Org. Chem., 2008, 73, 4750.
17 Neither decomposition nor decline of reactivity of
1-Me-AZADO+Clꢀ/1-Me-AZADO+BF4ꢀ has been observed after
storage in a desiccator at ambient temperature for several months.
18 Representative procedure for oxidation of primary alcohols to
carboxylic acids. To a stirring mixture of 3-phenylpropanol (7)
(150 mg, 1.10 mmol), sodium phosphate buffer (1.0 M, pH 6.8,
3.7 mL) in MeCN (3.7 mL), NaClO2 (80%) (375 mg, 3.3 mmol)
and 1-Me-AZADO+Clꢀ (11 mg, 55 mmol) was added. After
stirring for 0.5 h at 25 1C, 2-methyl-2-butene (1.5 mL) was added.
H2O (1 mL) was added and the mixture was extracted with Et2O.
Then the aqueous layer was adjusted to pH 2.0–3.5 with 10% HCl
and extracted twice with Et2O. The combined organic layer was
washed with acidic brine and then concentrated to give the crude
3-phenylpropanoic acid. The crude products were diluted by Et2O
and treated with CH2N2, followed by removal of excess CH2N2
and Et2O. Purification by column chromatography provided
methyl 3-phenylpropanoate (178 mg, 1.08 mmol, 98%).
3 K. Bowden, I. M. Heibron, E. R. H. Jones and B. C. L. Weedon,
J. Chem. Soc., 1946, 39.
4 E. J. Corey and G. Schmidt, Tetrahedron Lett., 1979, 5, 399.
5 M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J.
J. Grabowski and P. J. Reider, Tetrahedron Lett., 1998, 39, 5323.
6 P. H. J. Carlsen, T. Katsuki, V. S. Martin and K. B. Sharpless,
J. Org. Chem., 1981, 46, 3936.
7 M. Schroder and W. P. Griffith, J. Chem. Soc., Chem. Commun.,
¨
1979, 58.
8 R. Noyori, M. Aoki and K. Sato, Chem. Commun., 2003, 1977.
9 (a) H. Tohma, S. Takizawa, T. Maegawa and Y. Kita, Angew.
Chem., Int. Ed., 2000, 39, 1306; (b) H. Tohma, T. Maegawa,
S. Takizawa and Y. Kita, Adv. Synth. Catal., 2002, 344, 328.
10 P. L. Anelli, C. B. F. Montanari and S. Quici, J. Org. Chem., 1987,
52, 2559.
19 Procedure for oxidation of 2-(3,4-dimethoxyphenyl)ethanol on
large scale; To a stirring mixture of 2-(3,4-dimethoxyphenyl)ethanol
(6) (10 g, 55 mmol) and 1-Me-AZADO+Clꢀ (550 mg, 2.7 mmol)
in MeCN (90 ml) and sodium phosphate buffer (1.0 M, pH 6.8,
90 ml), NaClO2 (80%) (18.6 g, 165 mmol) was slowly added.
After stirring for 2 h at 25 1C, 2-methyl-2-butene (5 mL) was
added. H2O (10 mL) was added and the mixture was extracted with
AcOEt and was further purified with extraction using 5% NaOH.
The aqueous layer was washed with Et2O and acidified with 10%
HCl and then extracted with AcOEt. The organic layer
was evaporated and the crude products was recrystallized
from AcOEt–hexane to afford 3,4-dimethoxyphenylacetic acid
(9.26 g, 47.2 mmol, 86%) as colorless prisms.
11 J. B. Epp and T. S. Widlanski, J. Org. Chem., 1999, 64, 293.
12 (a) M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J.
J. Grabowski and P. J. Reider, J. Org. Chem., 1999, 64, 2564;
(b) M. Zhao, J. Li, E. Mano, Z. J. Song and D. M. Tschaen, Org.
Synth., 2004, 81, 195; (c) A. Zanka, Chem. Pharm. Bull., 2003, 51, 888.
13 Addition of small amount of NaOCl is essential for Merck’s
method since NaClO2 does not oxidize nitroxyl radicals effectively.
14 M. Shibuya, M. Tomizawa, I. Suzuki and Y. Iwabuchi, J. Am.
Chem. Soc., 2006, 128, 8412.
15 (a) A. E. de Nooy, A. C. Besemer and H. van Bekkum, Synthesis,
1996, 1153; (b) R. A. Sheldon and I. W. C. E. Arends, Adv. Synth.
Catal., 2004, 1051.
16 (a) V. Golubev, E. G. Roznzev and N. B. Neiman, Bull. Acad. Sci.
USSR, Div. Chem. Sci. (Engl. Transl.), 1965, 1989;
20 Y. Iwabuchi, J. Synth. Org. Chem. Jpn., 2008, 66, 1076.
ꢁc
This journal is The Royal Society of Chemistry 2009
Chem. Commun., 2009, 1739–1741 | 1741