Caprolactam → 4-Butoxybenzoyl caprolactam

HRID 1530790

반응식

HRID 1530790 반응식
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:16]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH3:19]>O1CCOCC1>[CH2:16]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:1]2=[O:8])=[O:26])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH3:19]

참가 물질

5

반응물 3

HCID 7768CaprolactamHCID 8471TriethylamineHCID 1185614-Butoxybenzoyl chloride

생성물 1

HCID 867564854-Butoxybenzoyl caprolactam수율 561.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To a 1 liter flask equipped with drying tube, condenser and overhead stirrer is charged 0.13 moles of caprolactam, 0.16 moles of triethylamine and 150 ml of dioxane. The resultant solution is heated to reflux, and a solution of 0.13 moles of 4-butoxybenzoyl chloride in 50 ml of dioxane is added over 15 minutes. The mixture is refluxed with stirring for 3 hours followed by stirring at room temperature for a further 18 hours. The mixture is filtered, and the solvent removed by rotary evaporation leaving a brown oil which is recrystallized from 25 ml of carbon tetrachloride to yield 0.73 moles of 4-butoxybenzoyl caprolactam which NMR shows to be 90% pure. The 4-butoxybenzoyl caprolactam has a melting point of approximately 87-92° C. 1H NMR reveals 0.9 ppm (t, 3H); 1.2-1.8 ppm (m, 12H); 2.7 ppm (m, 2H); 3.8 ppm (m, 2H); 4 ppm (t, 2H); 6.9 ppm (d, 2H); 7.5 ppm (d, 2H). 13C NMR provides 14 ppm (s); 20 ppm (s); 24 ppm (s); 29 ppm (d); 31 ppm (s); 39 ppm (s); 46 ppm (s); 68 ppm (s); 114 ppm (s); 128 ppm (s); 131 ppm (s); 162 ppm (s); 174 ppm (s); 178 ppm (s). IR (cm−1) at 2933, 1677, 1604, 1254.

후처리

  1. customTo a 1 liter flask equipped
  2. customwith drying tube, condenser and overhead stirrer
  3. temperatureto reflux
  4. temperatureThe mixture is refluxed
  5. stirringby stirring at room temperature for a further 18 hours
  6. filtrationThe mixture is filtered
  7. customthe solvent removed by rotary evaporation
  8. customleaving a brown oil which
  9. customis recrystallized from 25 ml of carbon tetrachloride

출처 및 근거

ORD 기록
ord-c1401ffffc88424783aa725dbc653453
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06197737B1

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