Acetic Anhydride → Ethyl 3-(4-acetoxyphenyl)-3-oxopropanoate

HRID 1779322Notes

Reaction equation

HRID 1779322 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[C:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[CH:14][CH:15]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 13136494Ethyl 3-(4-hydroxyphenyl)-3-oxopropanoate

Product 1

HCID 23282454Ethyl 3-(4-acetoxyphenyl)-3-oxopropanoateYield 93.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.85 grams of ethyl 4-hydroxybenzoylacetate was added to 15 ml of anhydrous pyridine. 0.91 grams of acetic anhydride was added along with a few crystals of dimethylaminopyridine (Aldrich). After 1 hour at room temperature the pyridine was removed exvacuo. The oily residue was stirred with 25 ml of water and 25 ml of ether. The aqueous phase was separated and extracted twice with 50 ml of ether. The combined ether extracts were washed with 0.5N HCl (25 ml), then with saturated sodium bicarbonate solution (25 ml), and finally with 25 ml of brine. The extracts were then dried with magnesium sulfate, filtered and the ether removed exvacuo. To yield 2.07 grams of ethyl 4-acetoxybenzoylacetate.

Workup

  1. customAfter 1 hour at room temperature the pyridine was removed exvacuo
  2. customThe aqueous phase was separated
  3. extractionextracted twice with 50 ml of ether
  4. washThe combined ether extracts were washed with 0.5N HCl (25 ml)
  5. dry with materialThe extracts were then dried with magnesium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2934a0a89a674db7b3f45e3e22e74f04
Source dataset
uspto-grants-1997_05
Patent number
US05627165

Reaction notes

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