Ethanol → Ethyl (2E)-4-oxo-4-phenyl-2-butenoate

HRID 982186Notes

Reaction equation

HRID 982186 reaction equation
[C:1](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14](O)[CH3:15].S(=O)(=O)(O)O.C(Cl)(Cl)Cl>O>[C:1](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 6212ChloroformHCID 676116Benzoylacrylic acid

Product 1

HCID 5369605Ethyl (2E)-4-oxo-4-phenyl-2-butenoateYield 92.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.50 g of trans-β-benzoylacrylic acid, 2.36 g of ethanol, 0.50 g of sulfuric acid and 30 ml of chloroform was refluxed for 5 hours while azeotropically removing water produced from the reaction system. After cooling, the reaction mixture was washed with a saturated solution of NaHCO and then with water. The solvent was distilled away to give 8.08 g of ethyl trans-β-benzoylacrylate.

Workup

  1. customproduced from the reaction system
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with a saturated solution of NaHCO
  4. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-7c57177a68ec4a73bbc59cd0fe46fe1a
Source dataset
uspto-grants-1991_02
Patent number
US04994600

Reaction notes

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