Methyl 4-Formylbenzoate → Methyl 4-(1-hydroxybutyl)benzoate

HRID 537434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537434
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[O:2].[CH2:13]([Mg]Br)[CH2:14][CH3:15]>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 15294Methyl 4-FormylbenzoateHCID 178455851HCID 178455851, Verbindung

Produkt 1

HCID 10443031Methyl 4-(1-hydroxybutyl)benzoateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of methyl 4-formylbenzoate (2.092 g, 12.74 mmol) in tetrahydrofuran (50 mL) was cooled to 0° C. To this solution was added n-propylmagnesium bromide (6.4 mL, 2.0M in THF) dropwise over 20 minutes. The reaction was stirred at 0° C. for 2 hours. The reaction was then quenched by addition of saturated ammonium chloride. This mixture was extracted with ethyl acetate twice. The organics were dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography (0-40% ethyl acetate in heptanes) gave (+/−)-methyl 4-(1-hydroxybutyl)benzoate (1.252 g, 47%) as a colorless oil. 1H NMR (400 MHz, CDCl3, δ): 7.97-8.02 (m, 2H), 7.40 (d, J=8.4 Hz, 2H), 4.74 (dd, J=7.8, 5.7 Hz, 1H), 3.90 (s, 3H), 1.61-1.82 (m, 2H), 1.23-1.49 (m, 2H), 0.92 (t, J=7.32 Hz, 3H).

Aufarbeitung

  1. customThe reaction was then quenched by addition of saturated ammonium chloride
  2. extractionThis mixture was extracted with ethyl acetate twice
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (0-40% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-b7ac043a425c4ebda596b7b4af2d979c
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859591B2

Notizen zur Reaktion

Wird geladen…