3-(2-Ethyl-4-formyl-6-methyl-phenyl)propenoic acid methyl ester → 3-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acid

HRID 1958772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958772
C[O:2][C:3](=[O:17])[CH:4]=[CH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH:13]=[O:14])=[CH:8][C:7]=1[CH2:15][CH3:16]>CO.[OH-].[Na+]>[CH2:15]([C:7]1[CH:8]=[C:9]([CH:13]=[O:14])[CH:10]=[C:11]([CH3:12])[C:6]=1[CH:5]=[CH:4][C:3]([OH:17])=[O:2])[CH3:16]

Komponenten

4

Edukt 1

HCID 765393103-(2-Ethyl-4-formyl-6-methyl-phenyl)propenoic acid methyl ester

Produkt 1

HCID 765393093-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acidAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A suspension of 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid methyl ester (5.93 g, 25.53 mmol) in MeOH (140 mL) and 2 N aq. NaOH (45 mL) was stirred at rt for 1 h. The MeOH was evaporated and the aq. solution was extracted twice with DCM. The aq. layer was acidified with 37% aq. HCl. The precipitate that formed was collected, washed with water and dried. The product was further purified by recrystallisation from EA (100 mL) to give 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid as yellow crystals (4.2 g). LC-MS: tR=0.87 min.

Aufarbeitung

  1. customThe MeOH was evaporated
  2. extractionthe aq. solution was extracted twice with DCM
  3. customThe precipitate that formed
  4. customwas collected
  5. washwashed with water
  6. customdried
  7. customThe product was further purified by recrystallisation from EA (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-2ca050fa7d4d4da981888b38f524133e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410151B2

Notizen zur Reaktion

Wird geladen…