3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester → 3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid

HRID 1665906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665906
C[O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH:13]=[O:14])=[CH:8][C:7]=1[CH3:15]>CO.[OH-].[Na+]>[CH:13]([C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([CH:5]=[CH:4][C:3]([OH:16])=[O:2])=[C:7]([CH3:15])[CH:8]=1)=[O:14]

Komponenten

4

Edukt 1

HCID 765393073-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester

Produkt 1

HCID 765393083-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester (2.9 g, 13.3 mmol) in methanol (70 mL), 2 N aq. NaOH (35 mL) is added. The suspension is stirred for 30 min at rt. Methanol is evaporated and the aq. solution is extracted twice with DCM. The aq. layer is acidified with 2 N aq. HCl and extracted twice with EA. The combined EA extracts are dried over MgSO4, filtered and evaporated. The crude product is recrystallized from EA to give 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid (2.2 g) as pale yellow crystals; LC-MS: tR=0.83 min; 1H NMR (D6-DMSO): δ 12.65 (s br, 1H), 9.92 (s, 1H), 7.66 (d, J=16.4 Hz, 1H), 7.61 (s, 2H), 6.12 (d, J=16.4 Hz, 1H), 2.35 (s, 6H).

Aufarbeitung

  1. customMethanol is evaporated
  2. extractionthe aq. solution is extracted twice with DCM
  3. extractionextracted twice with EA
  4. dry with materialThe combined EA extracts are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is recrystallized from EA

Quellen und Nachweise

ORD-Eintrag
ord-316e295907ca4a5ab777034fb2232d10
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039644B2

Notizen zur Reaktion

Wird geladen…