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 Morewebsite:http://www.uvchemkleys.com
Contact:+86 21 3868 0172
Address:RM-1203, Ziguang Building, #341 Shangcheng Road, Pudong Dist, Shanghai
Disynthesis Chemical Technology Co. Ltd.
Contact:+86-571-88194596
Address:Dengyun road 380, Gongshu district, Hangzhou city, China
Changsha Goomoo Chemical Technology Co.Ltd
Contact:+86-731-82197655
Address:No.649,Chezhan Rd.(N),Changsha,Hunan,China
Jiangsu Institute of Ecomones Co., Ltd
website:http://www.jsmone.com
Contact:+86-519-82821700
Address:95 Huanyuan N. Road, Jintan, Jiangsu, China
Shanghai Forever Biotech Co., Ltd.
Contact:+86-21-69734790
Address:Room 5017/5019、5022、5024 of Technology Innovation Centre, No.1155, Gongyuan East Rd, QingPu District, Shanghai 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)