Hydrochloric Acid → 2-Ethoxycarbonyl-3-phenylcyclohex-5-enone

HRID 1885982Notes

Reaction equation

HRID 1885982 reaction equation
[Na].[C:2]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].[CH:11](=O)/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(O)C>[CH2:9]([O:8][C:2]([CH:3]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH:11]=[CH:6][C:4]1=[O:5])=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 637511CinnamaldehydeHCID 5360545Sodium

Product 1

HCID 155814492-Ethoxycarbonyl-3-phenylcyclohex-5-enone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under a nitrogen atmosphere, 0.1 gram (0.004 mole) of sodium metal was reacted in 40 mL of ethanol. The solution was stirred, and 13.0 grams (0.100 mole) of ethyl acetoacetate was added. The reaction mixture was cooled in an ice bath, and 13.2 grams (0.100 mole) of trans-cinnamaldehyde in 10 mL of ethanol was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for about 18 hours. After this time the reaction mixture was saturated with gaseous hydrochloric acid and then was allowed to stand for about 65 hours. The reaction mixture was concentrated under reduced pressure to yield 2-ethoxycarbonyl-3-phenylcyclohex-5-enone. A 100% yield (24.4 grams) of product was assumed.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. additionUpon completion of addition
  3. stirringstirred for about 18 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa954fdf4cc1405caff67fea23cbf971
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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