71911-73-4

Basic information

• Product Name: ethyl C-<1-(ethoxycarbonyl)-2-oxocyclohexyl>malonate
• CAS NO: 71911-73-4
• Molecular Weight: 328.362
• Mol File: 71911-73-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl C-<1-(ethoxycarbonyl)-2-oxocyclohexyl>malonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl C-<1-(ethoxycarbonyl)-2-oxocyclohexyl>malonate(71911-73-4)
• EPA Substance Registry System: ethyl C-<1-(ethoxycarbonyl)-2-oxocyclohexyl>malonate(71911-73-4)

Safety Data

• Hazardous Substances Data: 71911-73-4(Hazardous Substances Data)

Upstream product

• 59736-20-8 ethyl 1-chloro-2-oxocyclohexanecarboxylate 
• 105-53-3 diethyl malonate 

Relevant articles and documents

Malonate Anion Induced Favorskii-Type Rearrangement. Reaction of Cyclic α-Halo Ketones with Sodiomalonates

The reaction of 2-chlorocyclohexanone (1b) with ethyl sodiomalonate in benzene at 0-25 deg C gave 6-bicyclohexan-6-ol (4c), the Favorskii-type intermediate, in 49percent yield, in place of the substitution product ethyl C-(2-oxocyclohexyl)malonate (3).Derivatives of bicycloheptan-7-ol (4a,b) and those of bicyclohexan-6-ol (4d,e) were also obtained in good yields by similar means.Compound 4c was transformed into 3 readily by heating with 0.05 equiv of NaH in benzene.The hydrolysis of 4a-d with 0.2 N NaOH followed by pyrolysis at 110-120 deg C gave the ring-contracted β-keto esters 9a-d.Pyrolysis after the hydrolysis with 2N NaOH gave the corresponding ketones 11a-d in good yields.Oxidation of 4c with CrO3 and HClO4 afforded ethyl C-(2-hydroxycyclopentanecarbonyl)malonate (14) in 45 percent yield.Treatment of 4c with Br2 gave ethyl C-(1-bromocyclopentanecarbonyl)malonate (18) in 64 percent yield.