Sodium Hydroxide → 3-Ethyl-3-(3-nitrophenyl)-4-pentenoic acid

HRID 397747Notes

Reaction equation

HRID 397747 reaction equation
[CH2:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)([CH:9]=[CH2:10])[CH2:4][C:5]([O:7]C)=[O:6])[CH3:2].[OH-].[Na+]>C(O)(C)C>[CH2:9]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)([CH:1]=[CH2:2])[CH2:4][C:5]([OH:7])=[O:6])[CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23000907Methyl 3-ethyl-3-(3-nitrophenyl)-4-pentenoate

Product 1

HCID 230010243-Ethyl-3-(3-nitrophenyl)-4-pentenoic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of methyl 3-ethyl-3-(3-nitrophenyl)-4-pentenoate (Preparation 59, assume 7.25 mmol) in isopropyl alcohol (9 ml) and 2M aqueous sodium hydroxide solution (4.4 ml, 8.75 mmol) was heated under reflux for 11 h, then the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The phases were separated and the organic extract was dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an oil which was used without further purification.

Workup

  1. temperatureunder reflux for 11 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe phases were separated
  5. extractionthe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89ff49498f134b0d84c637c9dce5d122
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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