Methyl 4-(3-hydroxyprop-1-ynyl)benzoate → Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester

HRID 131293

Reaktionsgleichung

Reaktionsgleichung von HRID 131293
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][CH2:2][CH:3]=[CH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

Komponenten

4

Edukt 1

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

Produkt 1

HCID 54205360Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysator2×HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(3-hydroxy-1-propinyl)benzoate (2 g) in methanol (32 mL) is added Lindlar catalyst (238 mg) and the mixture is stirred under hydrogen gas atmosphere at room temperature for 18 hours. To the reaction mixture is added Lindlar catalyst (90 mg) and the mixture is stirred for 1 hour. The reaction mixture is filtered to remove insoluble materials through Celite. The filtrate is concentrated in vacuo and the residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=100:0→50:50) to give methyl 4-(3-hydroxy-1-propenyl)-benzoate (1.5 g, yield; 75%) as an amorphous powder. MS (APCI) m/z; 175 [M+H−H2O]+

Aufarbeitung

  1. stirringthe mixture is stirred for 1 hour
  2. filtrationThe reaction mixture is filtered
  3. customto remove insoluble materials through Celite
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=100:0→50:50)

Quellen und Nachweise

ORD-Eintrag
ord-e57d3a1d53e74c51b6c551c135c5ef87
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384952B2

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