Potassium Hydroxide → 3-(3-Ethynylphenyl)propan-1-ol

HRID 658826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658826
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]#[C:12]C(C)(O)C)[CH:8]=[CH:9][CH:10]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[C:11]([C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:10]=[CH:9][CH:8]=1)#[CH:12]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 576085154-(3-(3-Hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol

Produkt 1

HCID 576083943-(3-Ethynylphenyl)propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-(3-(3-hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol (49) (0.750 g, 3.4 mmol) in toluene (50 mL) was added powdered KOH (0.390 g, 7 mmol). The resulting mixture was heated at reflux for 45 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to 10-15 mL volume and partitioned between EtOAc and water. The combined organics were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (15% EtOAc-hexanes) gave 3-(3-ethynylphenyl)propan-1-ol (50) as a light brown oil. Yield (0.272 g, 49%).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 45 min
  3. concentrationthe reaction mixture was concentrated under reduced pressure to 10-15 mL volume
  4. custompartitioned between EtOAc and water
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography (15% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ef2323d0fe7544779feb9d5db5c4759b
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076516B2

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