Ethanol → 3-(4-Methoxyphenyl)pentanedioic acid

HRID 904071Notes

Reaction equation

HRID 904071 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-9e247f3a31ec45c6bfb303f04119f955
Source dataset
uspto-grants-1980_10
Patent number
US04230621

Reaction notes

Loading…