Hydrochloric Acid → HCID 86732651, Verbindung

HRID 523334

Reaktionsgleichung

Reaktionsgleichung von HRID 523334
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Br[CH2:15][CH2:16][CH2:17][OH:18].C([O-])([O-])=O.[K+].[K+].Cl>CN1C(=O)CCC1>[OH:18][CH2:17][CH2:16][CH2:15][O:12][C:9]1[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:13])=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 92203Methyl p-coumarate

Produkt 1

HCID 86732651HCID 86732651, VerbindungAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

15 g (84.2 mmol) of 4-hydroxycinnamic acid methyl ester, 14 g (101 mmol) of 3-bromo-1-propanol, 23.4 g of K2CO3 are dissolved in 90 mL of NMP. The solution is heated up to 80° C. and stirred for 20 hours. Then, the reaction mixture is cooled down to room temperature and carefully acidified with 1N HCl solution. The solution is extracted with ethylacetate. The organic phase is dried over sodium sulfate, filtrated and concentrated under reduced pressure. Chromatography of the residue on silica gel using hexane:ethyl acetate 7:3 as eluent yielded 5.8 g of methyl (2E)-3-[4-(3-hydroxypropoxy)phenyl]prop-2-enoate as a white solid.

Aufarbeitung

  1. temperatureThen, the reaction mixture is cooled down to room temperature
  2. extractionThe solution is extracted with ethylacetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9f5c0ee6d1ee425da546ecc9bd12cda8
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334366B2

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