Hydrochloric Acid → Ethyl 3-oxo-3-(4-phenoxyphenyl)propanoate

HRID 1610454Notes

Reaction equation

HRID 1610454 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Mg+].[C:30]([O:36][CH2:37][CH3:38])(=[O:35])[CH2:31][C:32]([O-])=[O:33].Cl>O1CCCC1.O.C(OCC)(=O)C>[O:33]=[C:32]([C:14]1[CH:15]=[CH:16][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)[CH2:31][C:30]([O:36][CH2:37][CH3:38])=[O:35]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 195393-Phenoxybenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 178472271HCID 178472271, compound

Product 1

HCID 2760258Ethyl 3-oxo-3-(4-phenoxyphenyl)propanoateYield 180.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-phenoxybenzoic acid (13.5 g, 63.0 mmol) in tetrahydrofuran (150 ml) was added 1,1′-carbonylbis-1H-imidazole (11.2 g, 69.3 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction solution was added monoethyl malonate magnesium salt (10 g, 34.8 mmol) and the mixture was stirred at room temperature for 2 hrs. To the reaction solution were added ethyl acetate (50 ml) and water (50 ml), and conc. hydrochloric acid was added until the pH of the aqueous layer became acidic. The reaction solution was extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl 3-oxo-3-(4-phenoxyphenyl)propionate (17.9 g, 100%) as a brown oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. additionwas added until the pH of the aqueous layer
  3. extractionThe reaction solution was extracted with ethyl acetate (200 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c1aea9e0fce54cde85ead9f0ebb1c733
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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