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Thioglycolic Acid → [{1-(6-Methyl-1,3-benzodioxol-5-yl)ethyl}thio]acetic acid

HRID 1195259
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HRID 1195259 반응식
[SH:1][CH2:2][C:3]([OH:5])=[O:4].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[CH3:21][C:22]1[C:23]([CH:31](O)[CH3:32])=[CH:24][C:25]2[O:29][CH2:28][O:27][C:26]=2[CH:30]=1>C1C=CC=CC=1>[CH3:21][C:22]1[C:23]([CH:31]([S:1][CH2:2][C:3]([OH:5])=[O:4])[CH3:32])=[CH:24][C:25]2[O:29][CH2:28][O:27][C:26]=2[CH:30]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1133Thioglycolic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 145148961-(6-Methyl-1,3-benzodioxol-5-yl)ethanol

생성물 1

HCID 14514909[{1-(6-Methyl-1,3-benzodioxol-5-yl)ethyl}thio]acetic acid수율 93%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

3.7 g of mercaptoacetic acid and a catalytic amount of D-10-camphorsulfonic acid were added to 3.2 g of 1-(6-methyl-1,3-benzodioxol-5-yl)ethanol and the mixture was heated under reflux in 100 ml of benzene for 1 h. The reaction mixture was washed with water and then extracted with a 1 1Nsodium hydroxide solution. The aqueous layer was washed with ethyl acetate, acidified with 1Nhydrochloric acid and extracted with chloroform. The organic layer was dried over magnesium sulfate and the solvent was distilled off to obtain a crystalline residue. After recrystallization from diisopropyl ether, 4.2 g of the intended compound was obtained in the form of white crystals.

후처리

  1. temperaturethe mixture was heated
  2. washThe reaction mixture was washed with water
  3. extractionextracted with a 1 1Nsodium hydroxide solution
  4. washThe aqueous layer was washed with ethyl acetate
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customto obtain a crystalline residue
  9. customAfter recrystallization from diisopropyl ether

출처 및 근거

ORD 기록
ord-129ac101307246a3975f80d3d5ac4c8d
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05110956

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