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

HRID 1247671

Reaction equation

HRID 1247671 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-20bc1b6bef784024935ef71c58c9fb54
Source dataset
uspto-grants-2006_10
Patent number
US07129268B2

Linked notes

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