Iodine → (2-Ethyl-4-sulfanylphenoxy)acetic acid

HRID 1247671

Reaktionsgleichung

Reaktionsgleichung von HRID 1247671
P.II.C([O:6][C:7](=[O:22])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=O)=O)=[CH:12][C:11]=1[CH2:20][CH3:21])C.O>C(O)(=O)C>[CH2:20]([C:11]1[CH:12]=[C:13]([SH:16])[CH:14]=[CH:15][C:10]=1[O:9][CH2:8][C:7]([OH:22])=[O:6])[CH3:21]

Komponenten

6

Edukt 4

HCID 807IodineHCID 962WaterHCID 24404PhosphineHCID 21986343Ethyl 2-(4-(chlorosulfonyl)-2-ethylphenoxy)acetate

Produkt 1

HCID 17951787(2-Ethyl-4-sulfanylphenoxy)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a refluxing solution of PH3 (4.3 g, 126.5 mmol) and I2 (0.7 g, 2.6 mmol) in glacial acetic acid (30 ml) was added slowly a solution of (4-chlorosulfonyl-2-ethyl-phenoxy)-acetic acid ethyl ester (15 g, 48.9 mmol) in glacial acetic acid (20 ml). The reaction mixture was refluxed for 24 h. Water (10 ml) was added carefully and the mixture was refluxed for further 1 h after cooling, the reaction mixture was filtered and the filtrate diluted with water (100 ml). The mixture was extracted with dichloromethane (3×100 ml), and the organic phases were washed with water. After drying the dichloromethane phase was evaporated to give crude (2-ethyl-4-mercapto-phenoxy)-acetic acid in 10 g (96%) yield.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. temperaturethe mixture was refluxed for further 1 h
  3. temperatureafter cooling
  4. filtrationthe reaction mixture was filtered
  5. additionthe filtrate diluted with water (100 ml)
  6. extractionThe mixture was extracted with dichloromethane (3×100 ml)
  7. washthe organic phases were washed with water
  8. dry with materialAfter drying the dichloromethane phase
  9. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-20bc1b6bef784024935ef71c58c9fb54
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129268B2

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