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

HRID 1195310
ノート
印刷プレビュー

反応式

HRID 1195310 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, followed by the addition of 100 ml of benzene. The obtained mixture was heated under reflux for one hour, washed with water and extracted with a 1N aqueous solution of sodium hydroxide. The aqueous layer was washed with ethyl acetate, acidified with 1 N hydrochloric acid and extracted with chloroform. The organic layer was dried over magnesium sulfate and distilled to remove the solvent. The obtained crystalline residue was recrystallized from diisopropyl ether to obtain 4.2 g of the title compound as a colorless crystal.

後処理

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for one hour
  3. washwashed with water
  4. extractionextracted with a 1N aqueous solution of sodium hydroxide
  5. washThe aqueous layer was washed with ethyl acetate
  6. extractionextracted with chloroform
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe obtained crystalline residue was recrystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-b992a523cc424bdea0153ee848ef90ed
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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