Diethyl Ether → Ethyl 4-(4-chlorophenyl)-4-oxobut-2-enoate

HRID 1981872Notes

Reaction equation

HRID 1981872 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.S(OC)(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH2:28](OCC)[CH3:29]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]=[CH:9][C:10]([O:12][CH2:28][CH3:29])=[O:11])=[O:7])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 346434-(4-Chlorophenyl)-4-oxobut-2-enoic acid

Product 1

HCID 54524585Ethyl 4-(4-chlorophenyl)-4-oxobut-2-enoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.22 g of 3-(4-chlorobenzoyl)-acrylic acid in 40 ml of dimethylformamide were added 3.68 g of dimethyl sulfate and 1.36 g of potassium carbonate, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added diethyl ether. The mixture was washed, in turn, with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate. The diethyl ether was removed from the mixture by evaporation, and the residue was recrystallized from hexane to give 2.68 g of ethyl 3-(4-chlorobenzoyl)acrylate.

Workup

  1. washThe mixture was washed, in turn, with water
  2. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate
  3. customThe diethyl ether was removed from the mixture by evaporation
  4. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-723585dfc30a441eaedcd54918fb7303
Source dataset
uspto-grants-1986_06
Patent number
US04594197

Reaction notes

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