2-Allyl-5-methoxy-benzoic acid methyl ester → 5-Methoxy-2-propyl-benzoic acid methyl ester

HRID 2261781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261781
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH2:12][CH:13]=[CH2:14]>[Pd].CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH2:12][CH2:13][CH3:14]

Komponenten

4

Edukt 1

HCID 574433022-Allyl-5-methoxy-benzoic acid methyl ester

Produkt 1

HCID 574433035-Methoxy-2-propyl-benzoic acid methyl esterAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To an ambient temperature suspension of 10% palladium on carbon (245 mg) in MeOH (5 mL) is added a solution of 2-Allyl-5-methoxy-benzoic acid methyl ester (440 mg, 2.13 mmol) in MeOH (5 mL) in one portion. The reaction is placed under an atmosphere of hydrogen gas and is stirred overnight. The reaction mixture is filtered through Celite® and concentrated to yield the title compound (361 mg, 81%). 1H NMR (400 MHz, CDCl3) δ 7.38 (d, 1H, J=3.1 Hz), 7.15 (d, 1H, J=8.4 Hz), 6.97 (dd, 1H, J=8.6, 2.9 Hz), 3.89 (s, 3H), 3.82 (s, 3H), 2.88-2.82 (m, 2H), 1.65-1.53 (m, 2H), 0.95 (t, 3H, J=7.5 Hz).

Aufarbeitung

  1. filtrationThe reaction mixture is filtered through Celite®
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f40d981d04cd4dbca28e1de9541bb8da
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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