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

HRID 1195259
ノート
印刷プレビュー

反応式

HRID 1195259 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-129ac101307246a3975f80d3d5ac4c8d
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05110956

反応ノート

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