Pyridine → Cyclohexyl p-toluenesulfonate

HRID 128557

反応式

HRID 128557 の反応式
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.N1C=CC=CC=1>O>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 7966Cyclohexanol

生成物 1

HCID 13722Cyclohexyl p-toluenesulfonate収率 99.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Cyclohexanol (5.01 g, 50.0 mmol) and p-toluenesulfonyl chloride (10.6 g, 55.6 mmol) were charged into a 100 cc round-bottom flask, and then pyridine (20 ml) was added dropwise thereto under ice-cooling. The mixture was stirred for 8 hours while gradually elevating the temperature to room temperature. After completion of the reaction, cold water (500 ml) was added to the reaction mixture, and the mixture was extracted with ether (100 ml×3). The organic layers were combined, washed successively with 2N hydrochloric acid, water and a saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure to obtain substantially pure cyclohexyl p-toluenesulfonate as a white solid (12.7 g, 49.9 mmol, 99% yield).

後処理

  1. temperatureunder ice-cooling
  2. customto room temperature
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ether (100 ml×3)
  5. washwashed successively with 2N hydrochloric acid, water
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate
  7. customThe drying agent was separated by filtration
  8. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-6e8538f168ea4c70bab5f5b11227f36d
出典データセット
uspto-grants-1995_11
特許番号
US05464811

関連ノート

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