Ethyl Acetoacetate → 2-Ethoxycarbonyl-3-phenylcyclohex-5-enone

HRID 1885983Notes

Reaction equation

HRID 1885983 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Na].[CH:11](=O)/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C.C(OCC)(=O)CC(C)=O>[CH2:8]([O:7][C:1]([CH:2]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH:11]=[CH:5][C:3]1=[O:4])=[O:6])[CH3:9]

Participants

6

Reactant 3

HCID 8868Ethyl Acetoacetate2×HCID 637511CinnamaldehydeHCID 5360545Sodium2×

Product 1

HCID 155814492-Ethoxycarbonyl-3-phenylcyclohex-5-enoneYield 100%

Reagents, catalysts & solvents 2

HCID 8868Ethyl AcetoacetateCatalystHCID 702EthanolSolvent

Procedure

The reaction was repeated replacing the sodium metal with ethyl acetoacetate, sodium salt. Thus, 12.6 grams (0.097 mole) of ethyl acetoacetate, 0.5 gram (0.003 mole) of ethyl acetoacetate, sodium salt and 13.2 grams (0.100 mole) of trans-cinnamaldehyde in 50 mL of ethanol were reacted in a manner analogous to that of Example 6, Step A. A 100% yield (24.4 grams) of 2-ethoxycarbonyl-3-phenylcyclohex-5-enone was assumed.

Sources & evidence

ORD record
ord-545240a51ca748aba1adbeb7c5b90282
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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