Dipentaerythritol → Dipentaerythritol pentakis(3-mercaptobutyrate)

HRID 555208

反応式

HRID 555208 の反応式
[OH:1][CH2:2][C:3]([CH2:16][OH:17])([CH2:6][O:7][CH2:8][C:9]([CH2:14][OH:15])([CH2:12][OH:13])[CH2:10][OH:11])[CH2:4][OH:5].[SH:18][CH:19]([CH3:24])[CH2:20][C:21]([OH:23])=O.[OH2:25].C1(C)[CH:31]=[CH:30][C:29]([S:32](O)(=O)=O)=[CH:28]C=1.[C:37](=[O:40])([O-])O.[Na+]>C1(C)C=CC=CC=1>[SH:32][CH:29]([CH3:28])[CH2:30][C:31]([O:11][CH2:10][C:9]([CH2:14][OH:15])([CH2:8][O:7][CH2:6][C:3]([CH2:16][O:17][C:37](=[O:40])[CH2:20][CH:19]([SH:18])[CH3:24])([CH2:4][O:5][C:21](=[O:23])[CH2:20][CH:19]([SH:18])[CH3:24])[CH2:2][O:1][C:21](=[O:23])[CH2:20][CH:19]([SH:18])[CH3:24])[CH2:12][O:13][C:21](=[O:23])[CH2:20][CH:19]([SH:18])[CH3:24])=[O:25]

参加物

6

反応物 4

HCID 31352DipentaerythritolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate3 回HCID 99640843-Mercaptobutyric acid

生成物 1

HCID 87169359Dipentaerythritol pentakis(3-mercaptobutyrate)収率 13%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

A 500 ml three-necked flask was charged with 19.1 g (75 mmol) of dipentaerythritol (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), 54.1 g (450.0 mmol) of 3-mercaptobutanoic acid (manufactured by YODO KAGAKU CO., LTD.), 1.7 g (9.0 mmol) of p-toluenesulfonic acid monohydrate (manufactured by JUNSEI CHEMICAL CO., LTD.) and 300 g of toluene (manufactured by JUNSEI CHEMICAL CO., LTD.). A Dean-Stark apparatus and a condenser tube were attached. The materials were heated in an oil bath at 130° C. with stirring. After 1.5 hours after the reaction was initiated, 0.85 g (4.5 mmol) of p-toluenesulfonic acid monohydrate was added. Further, 1.7 g (9.0 mmol) of p-toluenesulfonic acid monohydrate was added after 4 hours from the initiation of the reaction. The reaction was carried out for another 2 hours. The reaction liquid was allowed to cool, was neutralized with 300 ml of a saturated aqueous sodium hydrogen carbonate solution, and was washed twice with 250 ml of pure water. The reaction liquid was then dehydrated and dried over anhydrous magnesium sulfate (manufactured by JUNSEI CHEMICAL CO., LTD.) and was distilled to remove the toluene, thereby giving a mixture containing the target compound. DP5MB obtained was a colorless transparent liquid and weighed 4.5 g, providing 13% yield. The composition formula of DP5MB was C30H52O12S5 and the molecular weight was 765.06.

後処理

  1. waitThe reaction was carried out for another 2 hours
  2. customThe reaction liquid
  3. temperatureto cool
  4. washwas washed twice with 250 ml of pure water
  5. customThe reaction liquid
  6. dry with materialdried over anhydrous magnesium sulfate (manufactured by JUNSEI CHEMICAL CO., LTD.)
  7. distillationwas distilled
  8. customto remove the toluene
  9. customgiving a mixture
  10. additioncontaining the target compound
  11. customDP5MB obtained
  12. customproviding 13% yield

出典と根拠

ORDレコード
ord-c194db9e4acf4b108d326bfde88da28a
出典データセット
uspto-grants-2011_11
特許番号
US08053167B2

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