Oxetane → 6-Phenyl-1-hexanol

HRID 483465

Reaktionsgleichung

Reaktionsgleichung von HRID 483465
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Mg].[O:12]1[CH2:15][CH2:14][CH2:13]1.[NH4+].[Cl-]>C1COCC1>[C:5]1([CH2:4][CH2:3][CH2:2][CH2:15][CH2:14][CH2:13][OH:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 10423OxetaneHCID 12503(3-Bromopropyl)benzeneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Produkt 1

HCID 5201106-Phenyl-1-hexanolAusbeute 33,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(3-Bromopropyl)benzene (20 g) in THF (75 ml) was added dropwise to magnesium (2.43 g) at a rate to maintain gentle reflux. The mixture was stirred for 2 h at RT and oxetane (10 g) was added dropwise. The resulting suspension was stirred at RT for 2 h and at reflux for 16 h and poured into saturated aqueous NH4Cl (100 ml). The mixture was extracted with ER (3×75 ml) and the dried extract was evaporated to leave a yellow oil. Distillation of the oil gave the title compound as a colourless liquid (6.05 g) b.p. 100°-105°/0.4 mmHg. T.l.c. [O] Rf 0.3.

Aufarbeitung

  1. temperatureto maintain gentle reflux
  2. stirringThe resulting suspension was stirred at RT for 2 h
  3. temperatureat reflux for 16 h
  4. extractionThe mixture was extracted with ER (3×75 ml)
  5. extractionthe dried extract
  6. customwas evaporated
  7. customto leave a yellow oil
  8. distillationDistillation of the oil

Quellen und Nachweise

ORD-Eintrag
ord-fd0fe6887c884a1698844305eaf9487d
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225445

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