2-Phenylpropanal → 1-Cyclohexyl-2-phenylpropanol

HRID 275820

Reaktionsgleichung

Reaktionsgleichung von HRID 275820
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1([CH:15]([CH3:18])[CH:16]=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOCC.C1COCC1>[CH:1]1([CH:16]([OH:17])[CH:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 71462-PhenylpropanalHCID 178478990HCID 178478990, Verbindung

Produkt 1

HCID 120942241-Cyclohexyl-2-phenylpropanolAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of cyclohexylmagnesium chloride (50 mmol) in 25 mL of Et2O and 40 mL of THF at −5° C. was added a solution of 2-phenylpropanaldehyde (5.36 g, 40 mmol) in 10 mL of THF. The reaction mixture exothermed to 5° C. After stirring at room temperature for 75 min, the solution was poured onto ice cold 1 N HCl, extracted with toluene, dried over MgSO4, and concentrated to give the title compound as a colorless oil (6.15 g, 70%):1H NMR (d6-DMSO): δ 7.23-7.30 (m, 2H, phenyl CH), 7.15-7.22 (m, 3H, phenyl CH), 4.17-4.51 (br s, 1H, —OH), 3.23-3.33 (m, 1H, R2CHOH), 2.78 (dq, J=7.0 Hz, J=7.1 Hz, 1H, —CH(CH3)Ph), 1.23-1.83 (m, 6H, cyclohexyl CH), 1.20 (d, J=6.9 Hz, 3H, —CH(CH3)Ph), 0.88-1.18 (m, 5H, cyclohexyl CH).

Aufarbeitung

  1. customexothermed to 5° C
  2. additionthe solution was poured onto ice cold 1 N HCl
  3. extractionextracted with toluene
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dd4e50a0e71f4518b38a4f582c247fd2
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353008B1

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