Benzyl Alcohol → Benzyl 6-bromohexanoate

HRID 843519

Reaktionsgleichung

Reaktionsgleichung von HRID 843519
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.N1C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Komponenten

5

Edukt 2

HCID 244Benzyl AlcoholHCID 898486-Bromohexanoyl chloride

Produkt 1

HCID 562258Benzyl 6-bromohexanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzyl 6-bromohexanoate was prepared by dropwise addition of a solution of 6-bromohexanoyl chloride (20.0 mL) in 100 mL of methylene chloride to a solution of 66.22 mL of benzyl alcohol in 60 mL of pyridine. The mixture was cooled using an ice-water bath for 90 min, then stirred at room temperature for 18 h. The solution was extracted with 200 mL of 1 N HCl followed by 2×150 mL of sat. NaHCO3. The extracts were discarded and the solution dried over Na2SO4. The solution was filtered and the solvent removed in vacuo to give an oil. This oil was purified on silica gel, eluting with a gradient of chloroform in hexanes. Fractions containing the product (TLC Rf 0.52, CHCl3/hexanes 6:4) were combined and the solvent removed to give 24.4 g.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customfor 90 min
  3. extractionThe solution was extracted with 200 mL of 1 N HCl
  4. dry with materialthe solution dried over Na2SO4
  5. filtrationThe solution was filtered
  6. customthe solvent removed in vacuo
  7. customto give an oil
  8. customThis oil was purified on silica gel
  9. washeluting with a gradient of chloroform in hexanes
  10. additionFractions containing the product (TLC Rf 0.52, CHCl3/hexanes 6:4)
  11. customthe solvent removed
  12. customto give 24.4 g

Quellen und Nachweise

ORD-Eintrag
ord-300d1ee73ce64b4bb9f8943f914f2bdb
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06379965B1

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