Diethyl Ether → Ethyl 4-oxo-4-(4-phenoxyphenyl)but-2-enoate

HRID 2418152Notes

Reaction equation

HRID 2418152 reaction equation
[O:1]([C:8]1[CH:20]=[CH:19][C:11]([C:12]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:31][CH3:32])(=O)=O.C(OCC)C>CN(C)C=O>[O:1]([C:8]1[CH:20]=[CH:19][C:11]([C:12]([CH:14]=[CH:15][C:16]([O:18][CH2:31][CH3:32])=[O:17])=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 54511907HCID 54511907, compound

Product 1

HCID 53776537Ethyl 4-oxo-4-(4-phenoxyphenyl)but-2-enoateYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.36 g of 3-(4-phenoxybenzoyl)acrylic acid were dissolved in 30 ml of dimethylformamide, and then 1.36 g of potassium carbonate and 3.08 g of diethyl sulfate were added. The mixture was stirred at room temperature for 3 hours. Diethyl ether was added to the reaction mixture, which was then washed, in turn, with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate. The diethyl ether was removed by evaporation under reduced pressure. The residue was purified first by silica gel column chromatography, eluted with a mixture of hexane and diethyl ether, then by recrystallization from hexane to give 4.36 g of ethyl 3-(4-phenoxybenzoyl)acrylate.

Workup

  1. washwas then 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 by evaporation under reduced pressure
  4. customThe residue was purified first by silica gel column chromatography
  5. washeluted with a mixture of hexane and diethyl ether
  6. customby recrystallization from hexane

Sources & evidence

ORD record
ord-ebe378ba6dbf411bb04f4fe072dfce5f
Source dataset
uspto-grants-1984_09
Patent number
US04472316

Reaction notes

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