Acetic Acid → Methyl [4-(aminomethyl)phenoxy]acetate acetate

HRID 733511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733511
O[N:2]=[CH:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.C(O)(=O)C.N#N>CO.[Pd]>[C:10]([OH:12])(=[O:11])[CH3:9].[NH2:2][CH2:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 947NitrogenHCID 73461790Methyl {4-[(hydroxyimino)methyl]phenoxy}acetate

Produkt 1

HCID 86028338Methyl [4-(aminomethyl)phenoxy]acetate acetateAusbeute 162,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl {4-[(hydroxyimino)methyl]phenoxy}acetate (30 g, 0.14 mol) in methanol (650 mL) was added glacial acetic acid (6.8 g) and passed N2 for 30 min. To this was added Pd/C (10%, 3 g) and hydrogenated under 2 bars of pressure for 12 h. The reaction mixture was concentrated under vacuum. The crude product was treated with EtOAc (500 mL) and the white product filtered off The solid was dried under vacuum to give the title compound (29 g, 81%).

Aufarbeitung

  1. customfor 30 min
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionThe crude product was treated with EtOAc (500 mL)
  4. filtrationthe white product filtered off The solid
  5. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fb2be3a7a0ff46b7897414ab1a99b24c
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589232B2

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