Sodium Hydroxide → 3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acid

HRID 1643696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643696
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:22][CH2:23][O:24][CH3:25])[C:12]=1[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:8]=[O:9].[OH-:26].[Na+]>CO.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:25][O:24][CH2:23][O:22][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:12]=1[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:8]([OH:26])=[O:9]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 866247663,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde

Produkt 1

HCID 667560413,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acidAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 3,5-bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde (220f) (42 g, 0.12 mol) in MeOH/H2O (500 mL) was added AgNO3 (21 g, 0.12 mol), followed by NaOH (15 g, 0.36 mol) in one portion at room temperature. The mixture was stirred at room temperature overnight and then filtered. The filtrate was concentrated under vacuum to remove MeOH. The residue was extracted with Et2O (2×100 mL) to remove impurities. The aqueous layer was acidified with conc. HCl to pH 4. The resulting white solid was filtered and dried under vacuum to give the title compound (31 g, 62% yield) as white solid.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customto remove MeOH
  4. extractionThe residue was extracted with Et2O (2×100 mL)
  5. customto remove impurities
  6. filtrationThe resulting white solid was filtered
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9d5d96b9c627411894929cfd51c6f9b5
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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