Ethyl Acetate → 1-Lauryl-2-pyrrolidone

HRID 61523

反応式

HRID 61523 の反応式
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]

参加物

10

反応物 4

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

生成物 1

HCID 624591-Lauryl-2-pyrrolidone収率 80%

試薬・触媒・溶媒 5

HCID 74236Tetrabutylammonium Bromide触媒HCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acid触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8078Cyclohexane溶媒

反応条件

温度
50 °C

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-7baa9a23c78d44c88ef74d641bd2c050
出典データセット
uspto-grants-2016_09
特許番号
US09441285B2

関連ノート

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