Sodium Hydroxide → [(6,7-Dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetic acid

HRID 371010노트

반응식

HRID 371010 반응식
C([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[C:18]([Cl:19])=[C:17]([Cl:20])[C:10]2[S:11][C:12]([CH:14]([OH:16])[CH3:15])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+]>C(O)C>[Cl:19][C:18]1[C:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])=[CH:8][C:9]2[CH:13]=[C:12]([CH:14]([OH:16])[CH3:15])[S:11][C:10]=2[C:17]=1[Cl:20]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 13290073Ethyl [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetate

생성물 1

HCID 13290074[(6,7-Dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetic acid수율 77.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To 16 g of ethyl[(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetate in 300 ml 95% ethanol is added 300 ml of a 6N sodium hydroxide and the mixture is refluxed at 100° for 30 mins. The cooled mixture is concentrated to a white slurry which is diluted with 200 ml of ice-water and 200 ml of ethyl ether. With stirring and efficient cooling, the mixture is acidified with 6N hydrochloric acid. The acidic mixture is extracted with ethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed. Recrystallization of the crude product from acetone and hexane gives 11.4 g of [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetic acid, mp 173°-175°.

후처리

  1. temperaturethe mixture is refluxed at 100° for 30 mins
  2. concentrationThe cooled mixture is concentrated to a white slurry which
  3. additionis diluted with 200 ml of ice-water and 200 ml of ethyl ether
  4. extractionThe acidic mixture is extracted with ethyl ether
  5. washThe ether extracts are washed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed
  9. customRecrystallization of the crude product from acetone and hexane

출처 및 근거

ORD 기록
ord-f80b40f8f57541e5ba343721b81dc9a5
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04528399

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