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

HRID 2418150Notes

Reaction equation

HRID 2418150 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:21](=O)([O-])[O-].[Li+].[Li+].CI.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][CH3:21])=[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 6328Methyl iodideHCID 11125Lithium CarbonateHCID 54511907HCID 54511907, compound

Product 1

HCID 53908224Methyl 4-oxo-4-(4-phenoxyphenyl)but-2-enoateYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.36 g of 3-(4-phenoxybenzoyl)acrylic acid were dissolved in 30 ml of dimethylformamide, then 1.48 g of lithium carbonate and 5.68 g of methyl iodide were added. The mixture was stirred at room temperature for 3 hours and then allowed to stand overnight. 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 then dried over magnesium sulfate. The diethyl ether was removed by evaporation under reduced pressure, and the residue was recrystallized from a mixture of benzene and hexane to give 5.24 g of methyl 3-(4-phenoxybenzoyl)acrylate.

Workup

  1. waitto stand overnight
  2. washwas then washed, in turn, with water
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over magnesium sulfate
  4. customThe diethyl ether was removed by evaporation under reduced pressure
  5. customthe residue was recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-6cd6d1e61ab5435283adc3cd4410dba4
Source dataset
uspto-grants-1984_09
Patent number
US04472316

Reaction notes

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