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

HRID 1903491
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HRID 1903491 반응식
C([O:5][C:6](=[O:24])[CH2:7][O:8][C:9]1[C:21]([Cl:22])=[C:20]([Cl:23])[C:12]2[S:13][C:14]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:15][C:11]=2[CH:10]=1)(C)(C)C.[OH-].[Na+]>C(O)C>[Cl:22][C:21]1[C:9]([O:8][CH2:7][C:6]([OH:24])=[O:5])=[CH:10][C:11]2[CH:15]=[C:14]([C:16]([OH:19])([CH3:18])[CH3:17])[S:13][C:12]=2[C:20]=1[Cl:23]
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HCID 14798Sodium HydroxideHCID 13290043t-Butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate

생성물 1

HCID 13290044[(6,7-Dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetic acid수율 93.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To 8.5 g of t-butyl[ [6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate in 200 ml of ethanol is added 150 ml of a 6 N sodium hydroxide solution and the mixture is refluxed at 100° for 30 mins. The cooled mixture is concentrated in vacuo 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 6 N hydrochloric acid. The acidic mixture is extracted with ethyl ether and the ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed. Recrystallization of the residue from acetone and pentane gives 6.8 g of [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetic acid, mp 194°-196°.

후처리

  1. temperaturethe mixture is refluxed at 100° for 30 mins
  2. concentrationThe cooled mixture is concentrated in vacuo 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 residue from acetone and pentane

출처 및 근거

ORD 기록
ord-5293e74031664b6a8c8c8b51cfb9c6dc
출처 데이터셋
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04436748

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