Green Chemistry
Paper
was cooled to room temperature. The reaction mixture was
stirred for 0.5 h in an open system, and then concentrated to
recover pure MeOH. To the residue was added MTBE (5 mL)
and diluted hydrochloric acid (1.0 M, 8 mL) to adjust the pH
to 2.0–3.0. Furthermore, the solution was partitioned into two
layers, and the aqueous phase was extracted with MTBE (5 mL
× 3). The combined organic layers were dried over anhydrous
Na2SO4, and concentrated in vacuo to give a solid, which was
purified via column chromatography on silica gel (eluent: pet-
roleum ether–ethyl acetate 15 : 1) to provide the desired vanil-
lin. White solid, 0.59 g (98%), m.p. 82–83 °C (lit.3a m.p.
80–81 °C); 1H NMR (400 MHz, CDCl3, ppm): δ 9.82 (br s,
1H), 7.43–7.41 (m, 2H), 7.04 (br d, J = 8.8 Hz, 1H), 6.30 (br s,
1H), 3.96 (s, 3H); 13C NMR (100 MHz, CDCl3, ppm): δ 191.1,
151.8, 147.2, 129.8, 127.6, 114.5, 108.9, 56.1; HRMS (ESI): m/z
[M − H+] calcd for C8H7O3 151.0395, found 151.0400. Gener-
ally, the purity of the recovered MeOH was more than 99% as
measured by GC, and the water content was less than 0.12% as
measured by the Karl Fischer method.
6 Selected examples for the oxidation of electron-donating
group-containing 4-cresols, see: (a) W. Baik, H. J. Lee,
J. M. Jang, S. Koo and B. H. Kim, J. Org. Chem., 2000,
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Acknowledgements
We gratefully acknowledge the National Natural Science Foun-
dation of China (Project no. 21176074) and the Research Fund
for the Doctoral Program of Higher Education of China
(Project no. 20130074110009) for financial support.
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Soc. Rev., 2009, 38, 3193; (b) J. A. Ashenhurst, Chem. Soc.
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