2,2-Dimethyl-5-phenyl-1,3-dioxane-4,6-dione → Methyl atropate

HRID 215691

Reaktionsgleichung

Reaktionsgleichung von HRID 215691
[I-].C[NH2+]C.C[C:6]1(C)O[C:10](=O)[CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8](=[O:19])[O:7]1>CO>[CH3:6][O:7][C:8](=[O:19])[C:9]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[CH2:10]

Komponenten

4

Edukt 2

HCID 848482,2-Dimethyl-5-phenyl-1,3-dioxane-4,6-dioneHCID 3016590Dimethylazanium iodide

Produkt 1

HCID 193334Methyl atropateAusbeute 102,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 25 g (135.1 mmol) N,N-dimethylammonium iodide and 11.91 g (54.1 mmol) 2,2-dimethyl-5-phenyl-[1,3]dioxane-4,6-dione in 585 ml abs. methanol was heated to 65° C. and the reaction was allowed to continue over night at 65° C. The reaction mixture was allowed to cool down to room temperature and the solvent was removed under reduced pressure. The residue was treated with diethyl ether, extracted with a satured NaHCO3 solution and brine and dried over MgSO4. The solvent was removed under reduced pressure and 9.01 g (quant.) of 2-phenyl acrylic acid methyl ester was isolated as a colourless oil. The compound was used without further purification.

Aufarbeitung

  1. waitto continue over night at 65° C
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was treated with diethyl ether
  4. extractionextracted with a satured NaHCO3 solution and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-669cd56648894d7da16df5c19ad75e04
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08192918B2

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