Ethanol → 3-(4-Methoxyphenyl)pentanedioic acid

HRID 1389042Notes

Reaction equation

HRID 1389042 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH:7]([CH:15](C(C)=O)[C:16]([O:18]CC)=[O:17])[CH:8](C(C)=O)[C:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(O)C.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]([CH2:15][C:16]([OH:18])=[O:17])[CH2:8][C:9]([OH:11])=[O:10])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86737067Ethyl 2,2'-(4-methoxybenzal)-bis-acetoacetate2×

Product 1

HCID 3472533-(4-Methoxyphenyl)pentanedioic acidYield 16.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2,2'-(4-methoxybenzal)bis-acetoacetate (30 g), ethanol (450 ml) and 50% sodium hydroxide (450 g) is refluxed vigorously for 1.0 hour. Water (150 ml) is added and most of the ethanol is removed by distillation in vacuo. The concentrate is acidified with concentrated hydrochloric acid and is extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried, evaporated and the residue is crystallized from benzene-methanol to afford 3.3 g of 3-(4-methoxyphenyl)glutaric acid, melting point 147°-150° C.

Workup

  1. temperatureis refluxed vigorously for 1.0 hour
  2. customis removed by distillation in vacuo
  3. extractionis extracted with ethyl acetate
  4. washThe ethyl acetate solution is washed with brine
  5. customdried
  6. customevaporated
  7. customthe residue is crystallized from benzene-methanol

Sources & evidence

ORD record
ord-87e0a650b3cd408a837a583b381a567a
Source dataset
uspto-grants-1981_01
Patent number
US04243608

Reaction notes

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