Acetic Acid → HCID 9815889, compound

HRID 917659Notes

Reaction equation

HRID 917659 reaction equation
[CH3:1][N:2]([CH3:20])[CH:3]1C=CCC[C:4]1([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(O)(=O)C.O.[OH-].[Na+]>C1CCCCC1>[CH3:20][N:2]([CH3:1])[CH2:3][CH:4]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 32329ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate

Product 1

HCID 9815889HCID 9815889, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

13.7 g (0.05 mol) of ethyl 2-dimethylamino-1-phenyl-3-cyclohexene-1-carboxylate (mixture of cis and trans isomers) [ethyl 3-dimethylamino-2-phenylpropionate content (HPLC): 1%], dissolved in 40 ml of cyclohexane, was refluxed with 3.0 g (0.05 mol) of acetic acid for 2 hours. After cooling, 30 ml of water were added. The two-phase mixture was made alkaline with sodium hydroxide solution. The aqueous phase was then separated off. The organic phase was washed with 30 ml of water and concentrated. 13.4 g (98%) of ethyl 2-dimethylamino-1-phenyl-3-cyclohexene-1-carboxylate isomer mixture of unchanged composition in respect of the cis/trans ratio were obtained with an ethyl 3-dimethylamino-2-phenyl-propionate content of 0.05% (HPLC).

Workup

  1. temperatureAfter cooling
  2. customThe aqueous phase was then separated off
  3. washThe organic phase was washed with 30 ml of water
  4. concentrationconcentrated
  5. addition13.4 g (98%) of ethyl 2-dimethylamino-1-phenyl-3-cyclohexene-1-carboxylate isomer mixture of unchanged composition in respect of the cis/trans ratio

Sources & evidence

ORD record
ord-f7df7614f68e48889f309dca72a61881
Source dataset
uspto-grants-2007_09
Patent number
US07273947B1

Reaction notes

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