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

HRID 982185Notes

Reaction equation

HRID 982185 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.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[C:1](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:19][CH3:20])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 94714Beta-benzoylacrylic acid

Product 1

HCID 5369605Ethyl (2E)-4-oxo-4-phenyl-2-butenoate

Conditions

Temperature
85 °C

Procedure

A mixture of 3.00 g of β-benzoylacrylic acid (cis/trans =1/2 according to 1H NMR analysis), 10 ml of ethanol and 0.63 g of sulfuric acid was refluxed for 2 hours. A pressure was gradually reduced with the aspirator and ethanol was distilled away for 10 minutes. After a pressure was finally reduced to 20 mmHg, the resultant was stirred at 85° C. for 40 minutes and then cooled, followed by the procedure as in Example 1 to give 2.45 g of ethyl trans-β-benzoylacrylate.

Workup

  1. temperaturewas refluxed for 2 hours
  2. distillationwas distilled away for 10 minutes
  3. temperaturecooled

Sources & evidence

ORD record
ord-3536ca34196848519ba0384e86fb2bec
Source dataset
uspto-grants-1991_02
Patent number
US04994600

Reaction notes

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