Water → Ethyl 4-(4-Methoxybenzyl)acetoacetate

HRID 2291875

Reaction equation

HRID 2291875 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](Cl)=[O:12])=[CH:5][CH:4]=1.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15]C(C)=O.[Na].O>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:12])[CH2:15][C:14]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 5360545SodiumHCID 109324413-(4-Methoxyphenyl)propionyl chloride

Product 1

HCID 9992286Ethyl 4-(4-Methoxybenzyl)acetoacetateYield 28%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-(4-Methoxyphenyl)propionyl chloride (84.6 g, 0.426 mole) was added to a stirred suspension of ethyl acetoacetate, sodium salt (64.7 g, 0.426 mole) in ether (250 ml) over a period of 1.5 hours and the reaction was allowed to sit for 16 hours. 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 under high vacuum to give the product as an yellow oil (30.0 g, 28%).

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 under high vacuum

Sources & evidence

ORD record
ord-74b8327ee5ab4f4cb4c30bb51a29a98e
Source dataset
uspto-grants-1989_01
Patent number
US04798843

Linked notes

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