Water → Ethyl 4-(4-methoxyphenyl)-3-oxobutanoate

HRID 2291873Notes

Reaction equation

HRID 2291873 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=[O:11])=[CH:5][CH:4]=1.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14]C(C)=O.[Na].O>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:11])[CH2:14][C:13]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 27346884-Methoxyphenylacetyl chlorideHCID 5360545Sodium

Product 1

HCID 14959491Ethyl 4-(4-methoxyphenyl)-3-oxobutanoateYield 20%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Methoxyphenylacetyl chloride (76 g, 0.413 mole) was added to a stirred suspension of ethyl acetoacetate, sodium salt (62.8 g, 0.413 mole) in ether (250 ml) over a period of 1.5 hours and the reaction was allowed to sit for 3 days. The reaction mixture was treated with water (100 ml) and extracted with ether. The ether extract was cooled in an ice bath and ammonia gas was bubbled into the solution for 2.5 hours while the reactants were allowed to warm to room temperature. The reaction was washed with water, filtered and the ether fraction was stirred with 3N hydrochloric acid (100 ml) for 16 hours. The ether layer was washed with water, 5% sodium bicarbonate, brine and dried with sodium sulfate. The solvent was removed and the residue was distilled on a kugelrohr apparatus to give the product as a yellow oil (19.7 g, 20%).

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. temperaturewas cooled in an ice bath
  4. customammonia gas was bubbled into the solution for 2.5 hours while the reactants
  5. washThe reaction was washed with water
  6. filtrationfiltered
  7. washThe ether layer was washed with water, 5% sodium bicarbonate, brine
  8. dry with materialdried with sodium sulfate
  9. customThe solvent was removed
  10. distillationthe residue was distilled on a kugelrohr apparatus

Sources & evidence

ORD record
ord-e148f649da9641b7bfcbbe39b2018f28
Source dataset
uspto-grants-1989_01
Patent number
US04798843

Reaction notes

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