酰氯在BaSO4，喹啉-S或硫脲鈍化的Pd催化劑的催化下氫化還原得到醛的反應(yīng)。如果不進(jìn)行鈍化，生成的醛會繼續(xù)還原成醇，因此可能的副產(chǎn)物有醇，酯和烷烴等。反應(yīng)常用的溶劑有甲苯、二甲苯、THF等等，通常要求嚴(yán)格無水條件下進(jìn)行，否則會有酸酐類副產(chǎn)物生成。硝基，鹵素，酯基等基團(tuán)在此反應(yīng)條件下不會被還原。

反應(yīng)機(jī)理

反應(yīng)實(shí)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 through 10 g of 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 over 5 g of 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年生于德國柏林。Otto Diels的學(xué)生，1906年獲得Ph.D.學(xué)位。1925年出任在基爾的藥物研究所的主任?！?/p>

參考文獻(xiàn)

1. Rosenmund, K. W. Ber. 1918, 51, 585–594.

2. Mosettig, E.; Mozingo, R. Org. React. 1948, 4, 362–377. (Review).

3. Tsuji, J.; Ono, K.; Kajimoto, T. Tetrahedron Lett. 1965, 6, 4565–4568.

4. Burgstahler, A. W.; Weigel, L. O.; Sch?fer, 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.

編譯自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Rosenmund reduction，page 525-526.