Acetophenone → 2-Phenyl-4-penten-2-ol

HRID 2037388

Reaktionsgleichung

Reaktionsgleichung von HRID 2037388
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C1COCC1>[C:4]1([C:1]([OH:3])([CH2:12][CH:11]=[CH2:10])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 7410AcetophenoneHCID 178455850HCID 178455850, Verbindung

Produkt 1

HCID 1437612-Phenyl-4-penten-2-olAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of acetophenone (30 g, 0.25 mol) in dry THF (250 mL) at −78° C. was added dropwise 1M allylmagnesium bromide (1.25 L, 1.25 mol). After addition was complete, the mixture was allowed to stir at rt for 3 h. The reaction was quenched with satd aq NH4Cl solution (30 mL). The mixture was extracted with EtOAc (200 mL). The organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated to give 2-phenylpent-4-en-2-ol (40.2 g), which was used for the next step without purification.

Aufarbeitung

  1. additionAfter addition
  2. customThe reaction was quenched with satd aq NH4Cl solution (30 mL)
  3. extractionThe mixture was extracted with EtOAc (200 mL)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-05c76fb37542473ebc45980deadbda82
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575156B2

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