Phenethyl bromide → 1,5-Diphenylpentan-3-ol

HRID 612536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612536
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Mg].[C:11]1([CH2:17][CH2:18][CH:19]=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)C>[C:4]1([CH2:3][CH2:2][CH:19]([OH:20])[CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 7666Phenethyl bromideHCID 7707BenzenepropanalHCID 5462224Magnesium

Produkt 1

HCID 128385101,5-Diphenylpentan-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

A solution of 2-(bromoethyl)benzene (1.73 g; 9.33 mmol) in diethylether (10 mL) was added to a stirred slurry of magnesium turnings (250 mg; 10.18 mmol) in 5 mL of ether. The reaction was initiated with a heat gun, and after the addition was complete the mixture was heated on an oil bath for 30 min. 3-Phenyl-1-propanal (1.25 g; 9.33 mmol) was added in 10 mL of ether, and reflux was continued for 1 hour. The reaction was cooled and quenched with saturated ammonium chloride, extracted into 2× ethyl acetate, and the combined organic portions were dried and concentrated. Chromatographic purification on a silica gel column (10% ethyl acetate in hexane) delivered 1.42 g (63%) of the diphenyl alcohol. 1H NMR (300 MHz, CDCl3): δ 1.84 (m, 4H); 2.61-2.76(m, 4H); 3.65 (m, 1H); 7.19-7.29 (m, 10H).

Aufarbeitung

  1. additionafter the addition
  2. temperaturewas heated on an oil bath for 30 min
  3. temperaturereflux
  4. temperatureThe reaction was cooled
  5. customquenched with saturated ammonium chloride
  6. extractionextracted into 2× ethyl acetate
  7. customthe combined organic portions were dried
  8. concentrationconcentrated
  9. customChromatographic purification on a silica gel column (10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-426555ab6994475ea761b4876325e1ea
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06004993

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