Methyl 4-(3-hydroxyprop-1-ynyl)benzoate → Methyl 4-(3-hydroxypropyl)benzoate

HRID 458995

Reaktionsgleichung

Reaktionsgleichung von HRID 458995
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][OH:13])=[CH:6][CH:5]=1>CCOC(C)=O.CO.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1

Komponenten

5

Edukt 1

HCID 4448596Methyl 4-(3-hydroxyprop-1-ynyl)benzoate

Produkt 1

HCID 14425137Methyl 4-(3-hydroxypropyl)benzoateAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester (12.65 g) in EtOAc (75 mL) and MeOH (75 mL) was hydrogenated at 50 psi on a Parr shaker in the presence of 10% palladium on carbon (2 g) for 24 h. The catalyst was removed by filtration through Celite® and the filtrate was concentrated. The reaction was repeated by adding 10% palladium on carbon (2 g) and hydrogenating on a Parr shaker for 24 h. After filtering through Celite®, the solution was concentrated in vacuo to provide 4-(3-hydroxy-propyl)-benzoic acid methyl ester (11.98 g).

Aufarbeitung

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated
  3. additionby adding 10% palladium on carbon (2 g)
  4. filtrationAfter filtering through Celite®
  5. concentrationthe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bac5b1d992734f90a9cc3a977a98c391
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192979B2

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