Potassium Hydroxide → Ketoprofen

HRID 1277785ノート

反応式

HRID 1277785 の反応式
CS[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](OC)([O:22]C)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)([CH3:8])[C:4]([O:6]C)=[O:5].[OH-].[K+]>[Zn].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O>[C:15]([C:11]1[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([OH:6])=[O:5])[CH:14]=[CH:13][CH:12]=1)(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

6

反応物 2

HCID 14797Potassium HydroxideHCID 12819452Methyl alpha-methylthio-alpha-(m-(alpha,alpha-dimethoxybenzyl)phenyl)propionate

生成物 1

HCID 3825Ketoprofen収率 85.4%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 24463Copper sulfate pentahydrate触媒HCID 962Water溶媒2 回

実験手順

Water (4 ml) was added to a mixture consisting of 269 mg of methyl α-methylthio-α-[m-(α,α-dimethoxybenzyl)phenyl]propionate, 500 mg of zinc powder and 80 mg of copper sulfate pentahydrate. Then, 500 mg of potassium hydroxide (85%) was added, and the mixture was stirred at the refluxing temperature for 44 hours. Water (4 ml) was further added, and with stirring, the mixture was heated under reflux for 3 hours. After cooling, the insoluble matter was separated by filtration, and washed with 20 ml of water. The filtrate and the washing were combined and adjusted to pH 1 with 2.0 ml of conc. hydrochloric acid. The mixture was stirred at 60° C. for 40 minutes and then, extracted three times with 20 ml of diethyl ether. The extract was washed with 10 ml of water, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using methylene chloride as an eluent to afford 162 mg of α-(m-benzoylphenyl)propionic acid in a yield of 85%.

後処理

  1. stirringwith stirring
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. temperatureAfter cooling
  5. customthe insoluble matter was separated by filtration
  6. washwashed with 20 ml of water
  7. stirringThe mixture was stirred at 60° C. for 40 minutes
  8. extractionextracted three times with 20 ml of diethyl ether
  9. washThe extract was washed with 10 ml of water
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was chromatographed on a silica gel column

出典と根拠

ORDレコード
ord-9f44d6b88f744f54bb96b681d67943cb
出典データセット
uspto-grants-1981_07
特許番号
US04278802

反応ノート

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