Sodium Hydroxide → [2,2'-Bithiophene]-3-acetic acid

HRID 2252268Notes

Reaction equation

HRID 2252268 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([O:9]CC)=[O:8])=[C:2]1[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.[OH-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=[O:8])=[C:2]1[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 85979007HCID 85979007, compound

Product 1

HCID 5150456[2,2'-Bithiophene]-3-acetic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 500 ml flask, 5.5 g (22 mmol) of ethyl (2,2′-bithiophene)-3-acetate dissolved in 50 ml of methanol was added, followed by 200 ml of 15% aqueous sodium hydroxide solution. The solution was refluxed for 3 hours. After cooling down the mixture to room temperature, the solution was concentrated via methanol removal using rotary evaporation. The aqueous solution was washed with diethyl ether, and then acidified with HCl to pH 1 upon which precipitation occurs. The white precipitate was dissolved in CH2Cl2 (150 ml×3) and the organic portion was collected. Chloroform was removed using a rotary evaporator after drying over magnesium sulfate to yield 4.7 g of white solid 96% yield. 1H-NMR (CDCl3): 7.34 (dd, 1H), 7.25 (d, 1H), 7.18 (dd, 1H), 7.08 (dd, 1H), 7.06 (d, 1H), 3.80 (s, 2H).

Workup

  1. additionwas added
  2. temperatureThe solution was refluxed for 3 hours
  3. concentrationthe solution was concentrated via methanol removal
  4. customevaporation
  5. washThe aqueous solution was washed with diethyl ether
  6. customacidified with HCl to pH 1 upon which precipitation
  7. dissolutionThe white precipitate was dissolved in CH2Cl2 (150 ml×3)
  8. customthe organic portion was collected
  9. customChloroform was removed
  10. customa rotary evaporator
  11. dry with materialafter drying over magnesium sulfate

Sources & evidence

ORD record
ord-b2deb87a1fa545ae88233e5969ca66f7
Source dataset
uspto-grants-2008_01
Patent number
US07321012B2

Reaction notes

Loading…