Carbon Dioxide → 4-(2-Methylphenoxy)butyl propiolate

HRID 1441155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441155
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].C(=O)(O)[O-].[Na+].C(=O)=O.[CH3:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21]Br>CO.CN(C)C=O>[C:1]([O:5][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:16]1[CH:23]=[CH:24][CH:25]=[CH:26][C:15]=1[CH3:14])(=[O:4])[C:2]#[CH:3]

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 10110Propiolic AcidHCID 516892Sodium BicarbonateHCID 47390421-(4-Bromobutoxy)-2-methylbenzene

Produkt 1

HCID 153350284-(2-Methylphenoxy)butyl propiolateAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 10 g of propiolic acid, 12 g of anhydrous sodium bicarbonate in 150 ml of anhydrous methanol was heated to 40° C. with stirring. When evolution of carbon dioxide ceased, the reaction mixture was cooled to a temperature 10° C. or less. The resultant precipitate was collected and dried under reduced pressure for two days. A mixture of 1 g of the sodium propiolate thus obtained and 2.64 g of 4-(2-methylphenoxy)butyl bromide in 30 ml of anhydrous N,N-dimethylformamide was heated at 110° C. under nitrogen atmosphere for four hours with stirring. After the reaction was completed, the reaction solution was poured into ice-water, and extracted twice with toluene. The combined toluene layer was washed successively with a saturated aqueous ammonium chloride solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained residue was subjected to silicagel column chromatography to yield 0.937 g of 4-(2-methylphenoxy)butyl propiolate (compound 10).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to a temperature 10° C. or less
  2. customThe resultant precipitate was collected
  3. customdried under reduced pressure for two days
  4. additionA mixture of 1 g of the sodium propiolate
  5. customthus obtained
  6. stirringwith stirring
  7. extractionextracted twice with toluene
  8. washThe combined toluene layer was washed successively with a saturated aqueous ammonium chloride solution
  9. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  10. customAfter removal of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-336f2835944d4211b2e619bf776b22d1
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05502242

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