Thioglycolic Acid → [{1-(1,3-Benzodioxol-5-yl)-1-methylpropyl}thio]acetic acid

HRID 2259786ノート

反応式

HRID 2259786 の反応式
[SH:1][CH2:2][C:3]([OH:5])=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27](O)([CH2:29][CH3:30])[CH3:28])=[CH:26][C:21]=2[O:20][CH2:19]1>C1C=CC=CC=1>[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]([S:1][CH2:2][C:3]([OH:5])=[O:4])([CH3:28])[CH2:29][CH3:30])=[CH:26][C:21]=2[O:20][CH2:19]1

参加物

5

反応物 3

HCID 1133Thioglycolic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 190016982-[3,4-(Methylenedioxy)phenyl]-2-butanol

生成物 1

HCID 14514927[{1-(1,3-Benzodioxol-5-yl)-1-methylpropyl}thio]acetic acid収率 35.4%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

50 ml of benzene, 1.29 g of mercaptoacetic acid and a catalytic amount of p-toluenesulfonic acid monohydrate were added to 2.27 g of 2-(1,3-benzodioxol-5-yl)-2-butanol (crude oil). The obtained mixture was heated under reflux for 11 hours and cooled, followed by the addition of benzene. The obtained mixture was washed with water, followed by the addition of a 1N aqueous solution of sodium hydroxide. The alkaline layer was separated, washed with ethyl acetate, acidified with concentrated hydrochloric acid and extrated with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled to remove the solvent. The residue was purified by silica gel column chromatography (chloroform) to obtain 1.11 g of the title compound as a colorless oil.

後処理

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 11 hours
  3. temperaturecooled
  4. washThe obtained mixture was washed with water
  5. additionfollowed by the addition of a 1N aqueous solution of sodium hydroxide
  6. customThe alkaline layer was separated
  7. washwashed with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationThe filtrate was distilled
  12. customto remove the solvent
  13. customThe residue was purified by silica gel column chromatography (chloroform)

出典と根拠

ORDレコード
ord-53646cb0981b4fea8f37799922f0d9e8
出典データセット
uspto-grants-1995_12
特許番号
US05475024

反応ノート

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