4-Bromobenzaldehyde → 1-(4-Bromophenyl)hexan-1-ol

HRID 606543

Reaktionsgleichung

Reaktionsgleichung von HRID 606543
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH3:5].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1>CCOCC>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 707414-BromobenzaldehydeHCID 178445865HCID 178445865, Verbindung

Produkt 1

HCID 126030861-(4-Bromophenyl)hexan-1-olAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

n-Pentylmagnesium bromide (12.1 mL of a 2.0 M solution in Et2O, 24.0 mmol) was added to a solution of 4-bromobenzaldehyde 5 (4.0 g, 22.0 mmol) at −78° C. The reaction was then warmed to room temperature for 0.5 h and quenched with saturated aqueous NH4Cl. The mixture was extracted with EtOAc and the organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 9:1 hex/EtOAc) gave 3.6 g (63%) of the alcohol 6 as a clear, colorless oil.

Aufarbeitung

  1. customquenched with saturated aqueous NH4Cl
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic portion was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ab7ddb1f963c451dbd59b9c1bb2cd033
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915316B2

Verknüpfte Notizen

Wird geladen…