Isobutyrophenone → 2-Methyl-1-phenyl-1-propanol

HRID 1086019

Reaktionsgleichung

Reaktionsgleichung von HRID 1086019
[BH4-].[Na+].[C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])[CH:4]([CH3:6])[CH3:5]>C(O)C>[CH3:5][CH:4]([CH3:6])[CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7]

Komponenten

4

Edukt 2

HCID 69144IsobutyrophenoneHCID 4311764Sodium borohydride

Produkt 1

HCID 956262-Methyl-1-phenyl-1-propanolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (6.5 g, 0.17 mol) was added in portions over a 2 h period to a solution of isobutyrophenone (50 g, 0.34 mol) in ethanol (150 mL) under nitrogen. The reaction mixture was stirred at room temperature for 2 h. Ethanol was removed under reduced pressure. The reaction mixture was added to water (100 mL) and extracted with methylene chloride (3×100 mL). The organic extract was collected, dried (anhy. MgSO4), and concentrated to give 2-methyl-1-phenyl-1-propanol (48 g, 94% yield): bp 62° C. at 0.1 mm; 1H NMR (CDC13) 0.75 (d, J=7, 3 H), 0.96 (d, J=7, 3 H), 1.98 (m, 1 H), 2.90 (bs, 1 H), 4.25 (d, J=7, 1 H), and 7.31 (s, 5 H).

Aufarbeitung

  1. customEthanol was removed under reduced pressure
  2. additionThe reaction mixture was added to water (100 mL)
  3. extractionextracted with methylene chloride (3×100 mL)
  4. extractionThe organic extract
  5. customwas collected
  6. customdried (anhy
  7. concentrationMgSO4), and concentrated

Quellen und Nachweise

ORD-Eintrag
ord-364f3b6e711f42359dae904977646017
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05012007

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