Ethyl Acetate → 1-Lauryl-2-pyrrolidone

HRID 61523

반응식

HRID 61523 반응식
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]

참가 물질

10

반응물 4

HCID 8857Ethyl AcetateHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 120252-Pyrrolidone2회

생성물 1

HCID 624591-Lauryl-2-pyrrolidone수율 80%

시약·촉매·용매 5

HCID 74236Tetrabutylammonium Bromide촉매HCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acid촉매HCID 962Water용매HCID 1140Toluene용매HCID 8078Cyclohexane용매

반응 조건

온도
50 °C

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-7baa9a23c78d44c88ef74d641bd2c050
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441285B2

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