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Sulfuric Acid → 4,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate

HRID 1440970
ノート
印刷プレビュー

反応式

HRID 1440970 の反応式
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:4][CH2:5][OH:6].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].S(=O)(=O)(O)O>N1C=CC=CC=1>[F:1][C:2]([F:11])([C:7]([F:8])([F:9])[F:10])[CH2:3][CH2:4][CH2:5][O:6][S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chlorideHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

生成物 1

HCID 220330274,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate収率 101.3%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

A solution of 17.3 g of 4,4,5,5,5-pentafluoropentanol in 40 ml of pyridine is mixed at 0° C. with 21 g of tosyl chloride and stirred for 3 hours at 0° C. For working up, the reaction mixture is added to 2 n sulfuric acid, extracted with diethyl ether, washed neutral with water, dried on sodium sulfate and concentrated by evaporation in a vacuum. 32.7 g of crude toluene-4-sulfonic acid-4,4,5,5,5-pentafluoropentyl ester is obtained as oil. The latter is dissolved in 300 ml of acetone and refluxed with 23 g of potassium thioacetate for 18 hours at 100° C. bath temperature. Then, it is mixed with water, extracted with diethyl ether, washed with water, dried on sodium sulfate, concentrated by evaporation in a vacuum and distilled. At 173°-177° C., 15 g of thioacetic acid-S-(4,4,5,5,5-pentafluoropentyl)-ester is obtained.

後処理

  1. extractionextracted with diethyl ether
  2. washwashed neutral with water
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

出典と根拠

ORDレコード
ord-2229528fc9a64cf7ae578a04748965bd
出典データセット
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05502046

反応ノート

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