Sodium Hydroxide → 4-Sulfothiophene-3-carboxylic acid

HRID 28011ノート

反応式

HRID 28011 の反応式
Cl[C:2]1[C:3]([C:7]([OH:9])=[O:8])=[CH:4][S:5][CH:6]=1.[OH-].[Na+].[S:12](=[O:15])([OH:14])[O-:13].[Na+]>[Cu]Cl.O>[S:12]([C:2]1[C:3]([C:7]([OH:9])=[O:8])=[CH:4][S:5][CH:6]=1)([OH:15])(=[O:14])=[O:13]

参加物

6

反応物 3

HCID 14798Sodium Hydroxide2 回HCID 134879204-Chlorothiophene-3-carboxylic acidHCID 23665763Sodium Bisulfite

生成物 1

HCID 166399174-Sulfothiophene-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

In a glass autoclave, 8.6 g. of 4-chlorothiophene-3-carboxylic acid are dissolved in 23 ml. of water containing 2.1 g. of sodium hydroxide, whereupon a solution of 5.6 g. of sodium bisulfite in 16 ml. of water is added and the solution made just alkaline with a 30% sodium hydroxide solution. The solution is treated with 0.43 g. of copper (I) chloride and heated at 143° C. for 16 hours. After cooling, the red copper oxide is filtered off under suction. The filtrate is acidified with 7 ml. of concentrated hydrochloric acid and the unreacted starting material precipitates out, the latter being removed by shaking out with ether. The acidic solution is treated with 12 g. of potassium chloride while warming and, after cooling to 0° C., the potassium salt of 4-sulfothiophene-3-carboxylic acid separates as colorless crystals. The crystals are dissolved in 50 ml. of water and the solution passed through an ion-exchange column which is charged with protons, after which the column is rinsed with water until the solution flowing out has a pH value of 5. The eluate is evaporated to dryness in vacuo. There is obtained 4-sulfothiophene-3-carboxylic acid as a crystalline residue of melting point 154° C. (recrystallization from water).

後処理

  1. additionThe solution is treated with 0.43 g
  2. temperatureAfter cooling
  3. filtrationthe red copper oxide is filtered off under suction
  4. customprecipitates out
  5. customthe latter being removed
  6. additionThe acidic solution is treated with 12 g
  7. temperatureof potassium chloride while warming
  8. dissolutionThe crystals are dissolved in 50 ml
  9. additionis charged with protons
  10. washafter which the column is rinsed with water until the solution
  11. customThe eluate is evaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-918f9bb244464f448d1cfed575217286
出典データセット
uspto-grants-1980_09
特許番号
US04224445

反応ノート

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