1-Bromo-3-chloropropane → 6-(3-Chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 2042628

Reaktionsgleichung

Reaktionsgleichung von HRID 2042628
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Produkt 1

HCID 220232326-(3-Chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a 500 mL round bottom flask, 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (10 g, 61.0 mmol), 1-bromo-3-chloro-propane (9.6 g, 61.0 mmol), and potassium carbonate (9.3 g, 67.1 mmol) in acetonitrile (300 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, separated, dried over MgSO4. Purification with silica gel chromatography eluting with hexanes/ethyl acetate (3:1) produced 10.6 g (73%). Mp 85-87° C. MS m/z 239 (M+H).

Aufarbeitung

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customPurification with silica gel chromatography
  8. washeluting with hexanes/ethyl acetate (3:1)
  9. customproduced 10.6 g (73%)

Quellen und Nachweise

ORD-Eintrag
ord-2a3ad35a01c24959933e317300ca6f8b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586588B2

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