Allyl bromide → 2-Allyl-cyclohexane-1,3-dione

HRID 437055

Reaktionsgleichung

Reaktionsgleichung von HRID 437055
[CH2:1](Br)[CH:2]=[CH2:3].[C:5]1(=O)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11].[OH-:13].[K+].[OH-].[Na+]>C(OCC)(=O)C>[CH2:1]([CH:5]1[C:6](=[O:11])[CH2:7][CH2:8][CH2:9][C:10]1=[O:13])[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 7841Allyl bromideHCID 130061,2-CyclohexanedioneHCID 14797Potassium HydroxideHCID 14798Sodium Hydroxide

Produkt 1

HCID 5660052-Allyl-cyclohexane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Allyl bromide (195 g., 1.62 mol.) was added over a 15 minute period to a stirred ice-cold mixture of cyclohexanedione (165 g., 1.47 mol.), copper-bronze (4.5 g.), and 330 ml. of 20% by weight aqueous potassium hydroxide. After 6 hours, the reaction was mixed with 1500 ml. of a 5% by weight aqueous sodium hydroxide solution and 1000 ml. of ethyl ether, filtered and the separated water layer acidified with 4 N aqueous hydrochloric acid to pH 1. A brown solid (188 g.) formed upon refrigeration at 0° C. The solid was taken up in ethyl acetate and the solution was washed with water (3× 150 ml.), dried (MgSO4), treated with charcoal, and condensed until turbid. Upon cooling, 126 g. (57%) of 2-allyl-1,3-cyclohexanedione was collected, m.p. 125°-127° C.

Aufarbeitung

  1. additionthe reaction was mixed with 1500 ml
  2. filtrationof ethyl ether, filtered
  3. customA brown solid (188 g.) formed upon refrigeration at 0° C
  4. washthe solution was washed with water (3× 150 ml.)
  5. dry with materialdried (MgSO4)
  6. additiontreated with charcoal, and condensed until turbid
  7. temperatureUpon cooling
  8. custom(57%) of 2-allyl-1,3-cyclohexanedione was collected

Quellen und Nachweise

ORD-Eintrag
ord-bce000b97f184c74b06ccd613eb4d512
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029674

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