Journal of Organic Chemistry p. 5048 - 5052 (1980)
Update date:2022-08-29
Topics:
Pittman, Charles U.
Liang, Yeon F.
Aldol condensation and hydrogenation of the condensation product have been carried out simultaneously by using an immobilized acid catalyst (Nafion-H or Amberlite IR-120) and Pd/C under hydrogen.Acetone was converted to 4-methyl-2-pentanone in a one-pot multistep process at 60-140 deg C and 20-300 psi of hydrogen.The yields of 4-methyl-2-pentanone were higher than the equilibrium-limited yields of mesityl oxide obtained in the absence of the hydrogenation catalyst, demonstrating that the equilibrium to mesityl oxide was shifted by mesityl oxide hydrogenation to 4-methyl-2-pentanone. 2-Propanol was the major byproduct because acetone hydrogenation was competitive with condensation.High-boiling products, found in aldol condensations, were not formed in the condensation-hydrogenation process.Use of RhCl(PPh3)3 or its polymer-bound analogue as the hydrogenation catalyst reduced the amount of acetone hydrogenation but slowed the condensation-hydrogenation reactions.The crossed aldol condensation-hydrogenation of benzaldehyde and acetone gave 4-phenyl-2-butanone with Nafion-H and Pd/C.The major side reaction was the competitive hydrogenation of benzaldehyde to toluene.The intramolecular condensation of 2,5-hexanedione gave mainly 2,5-dimethylfuran while the one-pot condensation-hydrogenation reaction gave 2,5-dimethyltetrahydrofuran.
View MoreShanghai AoBo Bio-Pharmaceutical Technology Co., Ltd.
Contact:+86-21-51320130-801, 816
Address:Room 601, No. 1011, Halei Road, Zhangjiang High-Tech Park, Pudong, Shanghai
Beijing Mediking Biopharm Co., Ltd.
Contact:+86-10-89753524/81760121/81769521
Address:Hongxianghong Incubator, Beiqijia Town, Changping district, Beijing, China
Changzhou Ruiping Chemical Co., Ltd
website:http://www.wishchem.com
Contact:+86-519-82324280
Address:No.288-1 Huacheng Road, Jintan
Wuhan Hanye Chemical New Material Co.,Ltd
Contact:+86-27-85308141
Address:LiuDian, Panlongcheng Economic Development Zone, HuangPi district, Wuhan, Hubei 430311 P.R.China
WUHAN CHEMPROSPECT PHARMTECH CO., LTD
website:http://www.chemprospect.com
Contact:+86--27-84984898
Address:No. 2, Road, East Lake Hi-tech Development Zone, Wuhan, China
Doi:10.1039/c3dt52188e
(2014)Doi:10.1021/jo00959a048
(1973)Doi:10.1246/bcsj.57.2266
(1984)Doi:10.1055/s-1994-25402
(1994)Doi:10.1021/acs.jmedchem.7b00241
(2017)Doi:10.1002/ejoc.201403441
(2015)