Water → 1-Acenaphtheneacetic acid

HRID 2230266Notes

Reaction equation

HRID 2230266 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][CH:6]1[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH:11]=[CH:10][CH:9]=[C:8]3[CH2:7]1)C.[OH-].[K+].O>CO>[CH:6]1([CH2:5][C:4]([OH:18])=[O:3])[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH:11]=[CH:10][CH:9]=[C:8]3[CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 13715672Ethyl2-(1,2-dihydro-1-acenaphthylenyl)acetate

Product 1

HCID 3445191-Acenaphtheneacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester obtained in Step C (1.9 g, 7.91.10−3 mol) is heated at reflux in the presence of potassium hydroxide (2.34 g, 4.17.10−2 mol, 5.3 eq.), water (16 ml) and methanol (16 ml) for one night. After evaporating off the solvent, the residue is taken up in water and extracted twice with ether. The basic aqueous phase is acidified using concentrated HCl in the cold state. The acid is extracted with ethyl acetate and dried over MgSO4. After evaporating off the solvent under reduced pressure, the title compound is obtained in the form of a yellow solid.

Workup

  1. customAfter evaporating off the solvent
  2. extractionextracted twice with ether
  3. extractionThe acid is extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. customAfter evaporating off the solvent under reduced pressure

Sources & evidence

ORD record
ord-05a60df93b1e44c8a9252e7aa4a4a5a4
Source dataset
uspto-grants-2002_07
Patent number
US06423870B1

Reaction notes

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