Ethanol → HCID 309391, compound

HRID 848564Notes

Reaction equation

HRID 848564 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:17])=[CH:11][C:12]([O:14]CC)=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)C.[OH-].[K+].O>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH3:17])=[CH:11][C:12]([OH:14])=[O:13])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 308933HCID 308933, compound

Product 1

HCID 309391HCID 309391, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 16.6 g. of ethyl 3-(4-nitrophenyl)-2-butenoate, 75 ml. of ethanol and 94.7 ml. of 1.5 N potassium hydroxide was heated on a steam bath for 70 minutes, and then it was cooled to room temperature. To the reaction mixture was added 200 ml. of water and 200 ml. of ethyl acetate. The aqueous phase was recovered and acidified with concentrated hydrochloric acid, and then the solid was recovered by filtration. This latter solid was recrystallized from aqueous ethanol to give 9.8 g. (67% yield) of the title compound, m.p. 167°-169° C.

Workup

  1. additionA mixture of 16.6 g
  2. additionTo the reaction mixture was added 200 ml
  3. customThe aqueous phase was recovered
  4. filtrationthe solid was recovered by filtration
  5. customThis latter solid was recrystallized from aqueous ethanol
  6. customto give 9.8 g

Sources & evidence

ORD record
ord-1086670fe422416ea229472027192803
Source dataset
uspto-grants-1981_10
Patent number
US04296129

Reaction notes

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