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Bromoacetic Acid → [{2-(1,3-Benzodioxol-5-yl)ethyl}thio]acetic acid

HRID 1195266
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1195266
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][SH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.Br[CH2:14][C:15]([OH:17])=[O:16].[OH-].[Na+]>C(O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][C:4]=2[O:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 158195122-(1,3-Benzodioxol-5-yl)ethanethiol

Produkt 1

HCID 19001624[{2-(1,3-Benzodioxol-5-yl)ethyl}thio]acetic acidAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

100 g of 2-(1,3-benzodioxol-5-yl)ethanethiol and 75.1 g of bromoacetic acid were dissolved in 1 l of ethanol. A solution of 44 g of sodium hydroxide in 125 ml of water and then 2 l of ethanol were added thereto. The mixture was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure. 2.5 l of water was added thereto. The mixture was made alkaline with a 1N sodium hydroxide solution, washed with 35% hydrochloric acid, extracted with ethyl acetate, washed with water four times and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 121 g of [{2-(1,3-benzodioxol-5-yl)ethyl}thio]acetic acid in the form of a faint yellow oil.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. addition2.5 l of water was added
  5. washwashed with 35% hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washwashed with water four times
  8. dry with materialdried over sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-50a05b120b5f4de2b89d0f4de1bc01e8
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05110956

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