Ethyl Acetate → 1-Lauryl-2-pyrrolidone

HRID 61523

Reaktionsgleichung

Reaktionsgleichung von HRID 61523
C([O-])([O-])=O.[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(OCC)(=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.OP(O)=O.O[Mo](O)(=O)=O.O.C1CCCCC1>[CH2:25]([N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Komponenten

10

Edukt 4

HCID 8857Ethyl AcetateHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 120252-Pyrrolidone2×

Produkt 1

HCID 624591-Lauryl-2-pyrrolidoneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acidKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Step A is conducted by adding tetrabutylammonium bromide (950 mg-3 mmol-0.05 eq.) and powder potash (23.1 g-411 mmol-7 eq.) under agitation to a solution of 2-pyrrolidinone (5.00 g-58.8 mmol) and bromododecane (18.5 mL, 76.4 mmol, 1.3 eq.) in toluene (60 mL). The mixture is heated to 50° C. overnight. After disappearance of the 2-pyrrolidinone (verified by TLC using a 4:1 v/v mixture of ethyl acetate and cyclohexane, and phosphomolybdic acid for detection) and cooling, 60 mL of water is added and the mixture left under agitation for a further 15 minutes. The aqueous and organic phases are separated and the aqueous phase is extracted once with diethylether (60 mL). The organic phases are combined, dried over Na2SO4, filtered and concentrated. After vacuum distillation (146° C.-0.5 mbars), N-dodecylpyrrolidin-2-one is obtained (Yield: 80%) for which the 1H and 13C NMR characterisations are as follows:

Aufarbeitung

  1. temperaturecooling
  2. customThe aqueous and organic phases are separated
  3. extractionthe aqueous phase is extracted once with diethylether (60 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationAfter vacuum distillation (146° C.-0.5 mbars)

Quellen und Nachweise

ORD-Eintrag
ord-7baa9a23c78d44c88ef74d641bd2c050
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441285B2

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