Cyclopentanol → Cyclopentyl 4-methylbenzene-1-sulfonate

HRID 21481

反応式

HRID 21481 の反応式
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[OH-].[K+]>CCOCC>[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 7298CyclopentanolHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium Hydroxide

生成物 1

HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonate収率 81.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Cyclopentanol (10 g, 0.116 mol), p-toluenesulfonyl chloride (24.8 g, 0.128 mol) and ether (100 ml) were charged into a 200 cc round-bottom flask and dissolved. Then, potassium hydroxide (32.5 g, 0.58 mol) in a powder form was added slowly thereto while cooling below 10° C. in a water bath. After addition, the mixture was stirred as it was for additional 2 hours. After completion of the reaction, the mixture was poured into ice-water (20 ml), and the organic layer and the aqueous layer were separated. The organic layer was dried, and concentrated under reduced pressure to obtain cyclopentyl p-toluenesulfonate as a pale yellow viscous liquid (22.0 g, 81.8% yield).

後処理

  1. dissolutiondissolved
  2. temperaturewhile cooling below 10° C. in a water bath
  3. additionAfter addition
  4. customAfter completion of the reaction
  5. customthe organic layer and the aqueous layer were separated
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-59bf7bd3f4e34541b45f75089796faf8
出典データセット
uspto-grants-1995_06
特許番号
US05424277

関連ノート

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