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3-(1,3-Benzodioxol-5-yl)prop-2-enoic acid → 3-Diethylamino-2,2-dimethylpropyl 3,4-methylenedioxycinnamate hydrochloride

HRID 268042
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 268042
[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=2[O:2]1.S(Cl)([Cl:17])=O.[CH2:19]([N:21]([CH2:28][CH3:29])[CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24]O)[CH3:20]>C1C=CC=CC=1>[ClH:17].[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][N:21]([CH2:28][CH3:29])[CH2:19][CH3:20])=[O:9])=[CH:4][C:3]=2[O:2]1
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Komponenten

5

Edukt 3

HCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acidHCID 24386Thionyl Chloride2×HCID 2959653-(Diethylamino)-2,2-dimethylpropan-1-ol

Produkt 1

HCID 681356293-Diethylamino-2,2-dimethylpropyl 3,4-methylenedioxycinnamate hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

3,4-METHYLENEDIOXYCINNAMIC ACID (15 G, 0.08 MOLE) WAS ADDED TO THIONYL CHLORIDE (30 ML) WITH RAPID STIRRING AND THEN REFLUXED FOR 3 HOURS. The mixture was stripped of excess thionyl chloride, benzene (100 ml) was added, and the mixture was again stripped of solvent. The residue was treated with a solution of 3-diethylamino-2,2-dimethylpropanol (12.8 g, 0.08 mole) in benzene (400 ml), refluxed for 3 hours, cooled, diluted with petroleum ether (500 ml) and stored overnight at room temperature. The benzene-petroleum ether solution was decanted, the residue dissolved in H2O (500 ml), adjusted to pH 10 with saturated aqueous K2CO3, and the product was extracted with CHCl3 (600 ml). The CHCl3 extract was dried overnight over MgSO4 and Darco, filtered, and the filtrate was stripped of solvent under reduced pressure. The product was dissolved in ether (800 ml) and the solution was adjusted to pH 2 with a solution of dry HCl in ether. The product crystallized with scratching and was collected by filtration. Yield: 18 g (61%). A sample was recrystallized from ethyl acetate, m.p. 152°-154°.

Aufarbeitung

  1. temperatureREFLUXED FOR 3 HOURS
  2. additionwas added
  3. temperaturerefluxed for 3 hours
  4. temperaturecooled
  5. customThe benzene-petroleum ether solution was decanted
  6. dissolutionthe residue dissolved in H2O (500 ml)
  7. extractionthe product was extracted with CHCl3 (600 ml)
  8. extractionThe CHCl3 extract
  9. dry with materialwas dried overnight over MgSO4 and Darco
  10. filtrationfiltered
  11. dissolutionThe product was dissolved in ether (800 ml)
  12. customThe product crystallized
  13. filtrationwas collected by filtration
  14. customA sample was recrystallized from ethyl acetate, m.p. 152°-154°

Quellen und Nachweise

ORD-Eintrag
ord-f942a9bd37164b26a7fe7a8add76e37a
Quelldatensatz
uspto-grants-1976_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03946042

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