3-Bromo-1-propanol → 3-[3-(Pentyloxy)phenoxy]propanol

HRID 36140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 36140
[H-].[Na+].[CH2:3]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:17][CH2:18][CH2:19][OH:20]>CN(C)C=O>[CH2:3]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:17][CH2:18][CH2:19][OH:20])[CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

5

Edukt 3

HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 156922293-(Pentyloxy)phenol

Produkt 1

HCID 224080143-[3-(Pentyloxy)phenoxy]propanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of 0.80 g of 60% NaH in 28 ml of anhydrous dimethylformamide is cooled in an ice bath. To this is added 3.01 g of the above 3-pentyloxyphenol oil dissolved in 7 ml of anhydrous dimethylformamide. This mixture is then stirred at room temperature for 45 minutes; 1.81 ml of 3-Bromopropanol are added; and the resultant mixture is stirred at 60° C. for 17 hours. The solvent is removed under vacuum, and the residue worked up in same manner as above. The residue obtained is flash chromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane:ether to yield 3-[3-(pentyloxy)phenoxy]propanol as a pale yellow oil.

Aufarbeitung

  1. temperatureis cooled in an ice bath
  2. customThe solvent is removed under vacuum
  3. customThe residue obtained
  4. customchromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane

Quellen und Nachweise

ORD-Eintrag
ord-23b48d1c4eb04d21a12c78419eafc48f
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412137

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