Rosenmund还原
反应机理
反应实例
【Synthesis 1976, 767–768】
【Helv. Chim. Acta 1990, 73, 405–410】
【Tetrahedron 2002, 58, 4851–4858】
【Org. Process Res. Dev. 2012, 16, 1607-1617】
A pressure vessel is charged in order with 600 mL of dry toluene,25 g. (0.30 mole) of anhydrous sodium acetate,3 g. of dry, 10% palladium-on-carboncatalyst,23 g. (0.10 mole) of 3,4,5-trimethoxybenzoyl chloride, and 1 mL of Quinoline S. The pressure vessel is flushed with nitrogen, sealed, evacuated briefly, and pressured to 50 p.s.i. with hydrogen. The mixture is shaken with 50 p.s.i. of hydrogen for 1 hour at room temperature, then heated at 35–40° for 2 hours. Agitation is continued overnight while the reaction mixture cools to room temperature. The pressure on the vessel is released, the vessel is opened, and the mixture is filtered through10 gof Celite filter aid, and the insoluble material is washed with 25 mL of toluene. The combined filtrates are washed successively with 25 mL of 5% sodium carbonate solution and 25 mL of water. The toluene solution is dried over5 gof anhydrous sodium sulfateand filtered. The filtrate is concentrated by distillation at reduced pressure using a water aspirator. The residue is distilledthrough a 10-cm. Vigreux column with warm watercirculating through the condenser, to preventcrystallization of the distillate, yielding 12.5–16.2 g (64–83%) of 3,4,5-trimethoxybenzaldehyde, b.p. 158–161°C(7–8 mmHg.), m.p. 74–75°C.
【Organic Syntheses, Coll. 1988，6，1007】
【Karl Wilhelm Rosenmund，1884年生于德国柏林。Otto Diels的学生，1906年获得Ph.D.学位。1925年出任在基尔的药物研究所的主任。】
参考文献
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3. Tsuji, J.; Ono, K.; Kajimoto, T. Tetrahedron Lett. 1965, 6, 4565–4568.
4. Burgstahler, A. W.; Weigel, L. O.; Schäfer, C. G. Synthesis 1976, 767–768.
5. McEwen, A. B.; Guttieri, M. J.; Maier, W. F.; Laine, R. M.; Shvo, Y. J. Org. Chem.1983, 48, 4436–4438.
6. Bold, V. G.; Steiner, H.; Moesch, L.; Walliser, B. Helv. Chim. Acta 1990, 73, 405–410.
7. Yadav, V. G.; Chandalia, S. B. Org. Proc. Res. Dev. 1997, 1, 226–232.
8. Chandnani, K. H.; Chandalia, S. B. Org. Proc. Res. Dev. 1999, 3, 416–424.
9. Chimichi, S.; Boccalini, M.; Cosimelli, B. Tetrahedron 2002, 58, 4851–4858.
10. Ancliff, R. A.; Russell, A. T.; Sanderson, A. J. Chem. Commun. 2006, 3243–3245.
11. Britton, H.; Catterick, D.; Dwyer, A. N.; Gordon, A. H.; et al. Org. Process Res. Dev.2012, 16, 1607-1617.
编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Rosenmund reduction，page 525-526.