Caprolactam → 4-Butoxybenzoyl caprolactam

HRID 275635

反応式

HRID 275635 の反応式
[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]

参加物

5

反応物 3

HCID 7768CaprolactamHCID 8471TriethylamineHCID 1185614-Butoxybenzoyl chloride

生成物 1

HCID 867564854-Butoxybenzoyl caprolactam収率 561.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-358cd28d54c44d9f90f27016086eafb2
出典データセット
uspto-grants-2002_03
特許番号
US06352562B1

関連ノート

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