Ethyl benzoylacetate → Ethyl 2-benzoyl-3-ethoxyacrylate

HRID 1677120Notes

Reaction equation

HRID 1677120 reaction equation
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]([O-])([O-])[O:16][CH2:17][CH3:18].C(OC(=O)C)(=O)C>O>[C:1]([C:9](=[CH:15][O:16][CH2:17][CH3:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 7918Acetic AnhydrideHCID 53630039Ethylorthoformate

Product 1

HCID 98006Ethyl 2-benzoyl-3-ethoxyacrylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Ethyl benzoylacetate (17.0 g, 88.4 mmol) and ethyl orthoformate (106 mL, 637 mmol) were dissolved in acetic anhydride (60.2 mL, 637 mmol) and stirred at 140° C. overnight. The reaction solution was returned to room temperature, then added with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (20.7 g, yield 94%) was obtained as an orange oil.

Workup

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified

Sources & evidence

ORD record
ord-8f59fb3422a2423d91c8c5d6264fae8e
Source dataset
uspto-grants-2011_08
Patent number
US08008306B2

Reaction notes

Loading…