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

HRID 1665916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665916
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 methanol (140 mL) and 2 N aq. NaOH (45 mL) is stirred at rt for 1 h. The methanol is evaporated and the aq. solution is extracted twice with DCM. The aq. layer is acidified with 37% aq. HCl. The precipitate that forms is collected, washed with water and dried. The product is further purified by recrystallisation from EA (100 mL) to give 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid (4.2 g) as yellow crystals; LC-MS: tR=0.87 min.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e523ec79ade6425ea3c5d5aaf5b89d44
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039644B2

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