Potassium Hydroxide → HCID 22139421, compound

HRID 1825795Notes

Reaction equation

HRID 1825795 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[OH-].[K+].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([OH:22])=[O:21]>O.[Cu]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Procedure

2-Methoxythiophenol (2.8 g, 20 mmol) was added to a solution of potassium hydroxide (4.6 g, 80 mmol) in water (50 ml) and the mixture was degassed for 15 minutes. 2-Iodophenylacetic acid (5.24 g, 20 mmol) and copper bronze (64 mg, 1 mmol) were then added to the reaction mixture, which was refluxed overnight. The solution was cooled down, filtered and the precipitate washed with water (50 ml). The filtrate was acidified with conc HCl (pH 1), extracted with dichloromethane (3×100 ml). The organics were combined, extracted with saturated brine, dried over sodium sulphate and evaporated in vacuo to give the title compound as a pale brown oil which solidified overnight. The compound was used without any further purification (5.10 g, 93%).

Workup

  1. customthe mixture was degassed for 15 minutes
  2. temperaturewas refluxed overnight
  3. temperatureThe solution was cooled down
  4. filtrationfiltered
  5. washthe precipitate washed with water (50 ml)
  6. extractionextracted with dichloromethane (3×100 ml)
  7. extractionextracted with saturated brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d2f269f4293c4a63bc17e80052079a0c
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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