Isoprene → 2,2-Dimethyl-3-isopropenylcyclobutanone

HRID 1855738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855738
[CH2:1]=CC(=C)C.CN(C)C(=O)C(C)C.C(N(CC)CC)C.[CH3:21][C:22]1([CH3:30])[C:25](C)([CH:26]=[CH2:27])[CH2:24][C:23]1=[O:29]>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH3:30][C:22]1([CH3:21])[CH:25]([C:26]([CH3:27])=[CH2:1])[CH2:24][C:23]1=[O:29]

Komponenten

7

Edukt 4

HCID 6557IsopreneHCID 8471TriethylamineHCID 243415N,N,2-trimethylpropanamideHCID 233484532,2,3-Trimethyl-3-vinyl-cyclobutanone

Produkt 1

HCID 233484522,2-Dimethyl-3-isopropenylcyclobutanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

34.0 g (0.5 mol) of isoprene and then, at 0°-10° C., 75.0 g (0.55 mol) of zinc chloride were added to 350 ml of the solution, prepared according to Example 1, of the amide chloride is isobutyric acid dimethylamide in methylene chloride, while cooling and stirring. Thereafter, 50.0 g (0.5 mol) of triethylamine were added dropwise at the same temperature and, after warming to 20°-25° C., the mixture was heated to reflux and worked up according to Example 2. This gave 40.4 g (58%, relative to isobutyric acid dimethylamide employed) of the ketone of boiling point 109°-110° C./100 mm Hg and nD20 of 1.4518 (contaminated to the extent of about 10% by 2,2,3-trimethyl-3-vinyl-cyclobutanone).

Aufarbeitung

  1. customprepared
  2. temperaturewhile cooling
  3. temperatureafter warming to 20°-25° C.
  4. temperaturethe mixture was heated
  5. temperatureto reflux

Quellen und Nachweise

ORD-Eintrag
ord-40269d29d5204e60b3c2cbde4e815d32
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04216172

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