Ethyl Acetate → 3-(3-METHOXY-PHENYL)-2-METHYL-PROPIONIC ACID

HRID 323778Notes

Reaction equation

HRID 323778 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:14]C)[C:6]2=[O:13].C([O-])(=[O:18])C.[Na+].CCOC(C)=O>C(O)(=O)C>[CH3:12][O:11][C:8]1[CH:7]=[C:3]([CH2:4][CH:5]([CH3:14])[C:6]([OH:13])=[O:18])[CH:2]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 105398944-Bromo-2-ethyl-7-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 105839593-(3-METHOXY-PHENYL)-2-METHYL-PROPIONIC ACIDYield 73.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the indanone (5c, 29.7 g, 0.110 mol), sodium acetate (15.0 g, 0.183 mol), 10% palladium-coal (3.01 g) in acetic acid (300 ml) was hydrogenated at atmospheric pressure. The catalyst was filtered off and the solvent evaporated. The residue was partitioned between water and AcOEt and the aqueous layer was extracted with AcOEt. The combined organic layers were washed with water, 5% NaHCO3 and brine, dried, filtered and evaporated. The crude product was purified by recrystallization from hexane:AcOEt to give the pure titled compound (15.7 g, 3 steps yield 51%), mp, 67-69° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. customThe residue was partitioned between water and AcOEt
  4. extractionthe aqueous layer was extracted with AcOEt
  5. washThe combined organic layers were washed with water, 5% NaHCO3 and brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by recrystallization from hexane

Sources & evidence

ORD record
ord-f3c13ddbcc63412d9f5e818fb0f17fde
Source dataset
uspto-grants-2001_04
Patent number
US06214876B1

Reaction notes

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