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

HRID 982182Notes

Reaction equation

HRID 982182 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 676116Benzoylacrylic acid

Product 1

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

Conditions

Temperature
62 °C

Procedure

A mixture of 7.75 g of trans-β-benzoylacrylic acid, 25.8 ml of ethanol and 1.63 g of sulfuric acid was stirred at 62° C. for 3 hours. A pressure was gradually reduced with the aspirator and ethanol was distilled away for 20 minutes. After a pressure was finally reduced to 20 mmHg, the resultant was stirred at 62° C. for 1.5 hours and then cooled, followed by the procedure as in Example 1 to give 8.18 g of ethyl trans-β-benzoylacrylate.

Workup

  1. distillationwas distilled away for 20 minutes
  2. stirringthe resultant was stirred at 62° C. for 1.5 hours
  3. temperaturecooled

Sources & evidence

ORD record
ord-dfe4d892e62f4aa1b8794a93070eb1fd
Source dataset
uspto-grants-1991_02
Patent number
US04994600

Reaction notes

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