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Water → [{1-(6-Methyl-1,3-benzodioxol-5-yl)propyl}thio]acetic acid

HRID 2259734
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2259734
[CH3:1][C:2]1[C:3]([CH:11](O)[CH2:12][CH3:13])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[SH:15][CH2:16][C:17]([OH:19])=[O:18].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]1[C:3]([CH:11]([S:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:12][CH3:13])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 1133Thioglycolic AcidHCID 145148971-(6-Methylbenzo[d][1,3]dioxol-5-yl)propan-1-ol

Produkt 1

HCID 14514911[{1-(6-Methyl-1,3-benzodioxol-5-yl)propyl}thio]acetic acidAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysator
HCID 241
Benzene
Lösungsmittel

Versuchsvorschrift

2.27 g of 1-(6-methyl-1,3-benzodioxol-5-yl)-1-propanol, 0.1 g of p-toluenesulfonic acid and 1.52 g of mercaptoacetic acid were dissolved in 80 ml of benzene. The solution was heated under reflux for 12 h while water was removed. The reaction mixture was poured into water. The aqueous layer was made alkaline and washed with ether. The aqueous layer was then acidified and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to obtain a faint yellow solid. It was purified according to silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.83 g of the intended compound in the form of white crystals.

Aufarbeitung

  1. temperatureThe solution was heated
  2. customwas removed
  3. additionThe reaction mixture was poured into water
  4. washwashed with ether
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a faint yellow solid
  10. customIt was purified

Quellen und Nachweise

ORD-Eintrag
ord-3a44ec49b5484347ae007131d0a738f2
Quelldatensatz
uspto-grants-1995_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05475024

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