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

HRID 2259786

반응식

HRID 2259786 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-53646cb0981b4fea8f37799922f0d9e8
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05475024

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