Ethanol → 3-(4-Nitrophenyl)-3-phenylprop-2-enoic acid

HRID 66616Notes

Reaction equation

HRID 66616 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[CH:8][C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[OH-].[K+]>O>[C:1]1([C:7]([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[CH:8][C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 308955Ethyl 3-(4-nitrophenyl)-3-phenylprop-2-enoate

Product 1

HCID 534276003-(4-Nitrophenyl)-3-phenylprop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 62.5 g. of ethyl 3-phenyl-3-(4-nitrophenyl)propenoate, 100 ml. of ethanol and 300 ml. of 1.5 N potassium hydroxide was heated on a steam bath for 1 hour. To the cooled reaction mixture was added 800 ml. of water and 500 ml. of ethyl acetate, and then the ethyl acetate layer was removed. The aqueous layer was acidified, and the solid which precipitated was collected by filtration. This solid was recrystallized from toluene and then from carbon tetrachloride to give 22 g. of the title compound, m.p. 188°-189° C.

Workup

  1. additionA mixture of 62.5 g
  2. customTo the cooled reaction mixture
  3. additionwas added 800 ml
  4. customof ethyl acetate, and then the ethyl acetate layer was removed
  5. customthe solid which precipitated
  6. filtrationwas collected by filtration
  7. customThis solid was recrystallized from toluene
  8. customfrom carbon tetrachloride to give 22 g

Sources & evidence

ORD record
ord-6a40409b9a434d75b84f38b1cb98758d
Source dataset
uspto-grants-1982_08
Patent number
US04342781

Reaction notes

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