Estragole → Chavicol

HRID 1416428

Reaktionsgleichung

Reaktionsgleichung von HRID 1416428
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]=[CH2:11])=[CH:5][CH:4]=1.B(Br)(Br)Br.[B]>C(Cl)Cl>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1)[CH:10]=[CH2:11]

Komponenten

5

Edukt 3

HCID 8815EstragoleHCID 25134Boron tribromideHCID 5462311Boron

Produkt 1

HCID 68148ChavicolAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 50.01 g (337.4 mmol) of 1-methoxy-4-(2-propenyl)benzene (Aldrich Chemical Company, Milwaukee, Wis.) dissolved in 300 mL of anhydrous methylene chloride was added dropwise 375 mL (375 mmol) of 1.0M boron tribromide (Aldrich) in methylene chloride. The reaction was run under nitrogen at room temperature and the mixture was stirred for 1 hour. The mixture was poured over 1000 mL of crushed ice, stirred for 5 minutes, and transferred to a separatory funnel. The organic layer was drained and saved. The boron salts were transferred to a filter containing Celite™ (Aldrich Chemical Co., Milwaukee, Wis.) and the filter containing the salts was washed with portions of methylene chloride and then water. The filtrate was transferred to a separatory funnel and the organic and aqueous layers were separated. The aqueous layer was extracted with four 100-mL portions of methylene chloride. The methylene chloride solutions were pooled, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 25.27 g (56%) of crude 4-(2-propenyl)phenol. The crude product was distilled twice at reduced pressure to yield 20.34 g (45%) of 4-(2-propenyl)phenol. The NMR data was consistent with that reported by Rajashekhar and coworkers (J. Biol. Chem. 1984, 259, 6925).

Aufarbeitung

  1. customwas run under nitrogen at room temperature
  2. stirringstirred for 5 minutes
  3. customtransferred to a separatory funnel
  4. additioncontaining Celite™ (Aldrich Chemical Co., Milwaukee, Wis.)
  5. additionthe filter containing the salts
  6. washwas washed with portions of methylene chloride
  7. customThe filtrate was transferred to a separatory funnel
  8. customthe organic and aqueous layers were separated
  9. extractionThe aqueous layer was extracted with four 100-mL portions of methylene chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ed57516284ab4228ba158133aee6af22
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912377

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