Ethyl Acetate → 1-Lauryl-2-pyrrolidone

HRID 61523

Reaction equation

HRID 61523 reaction equation
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]

Participants

10

Reactant 4

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

Product 1

HCID 624591-Lauryl-2-pyrrolidoneYield 80%

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acidCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
50 °C

Procedure

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:

Workup

  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)

Sources & evidence

ORD record
ord-7baa9a23c78d44c88ef74d641bd2c050
Source dataset
uspto-grants-2016_09
Patent number
US09441285B2

Linked notes

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