Ethyl Acetate → 3-(3-Methoxyphenyl)-2-methylpropanoic acid

HRID 323778ノート

反応式

HRID 323778 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 105839593-(3-Methoxyphenyl)-2-methylpropanoic acid収率 73.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f3c13ddbcc63412d9f5e818fb0f17fde
出典データセット
uspto-grants-2001_04
特許番号
US06214876B1

反応ノート

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