Ethylene Glycol → 4-(Benzo(b)thienyl)acetic acid

HRID 2390968Notes

Reaction equation

HRID 2390968 reaction equation
C(O)CO.[S:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH:14](C#N)[C:15]([O:17]C(C)(C)C)=[O:16])[C:8]=2[CH:7]=[CH:6]1.[OH-].[K+].O>C1(C)C=CC=CC=1>[S:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH2:14][C:15]([OH:17])=[O:16])[C:8]=2[CH:7]=[CH:6]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 14797Potassium HydroxideHCID 66751041HCID 66751041, compound

Product 1

HCID 758334-(Benzo(b)thienyl)acetic acidYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To ethylene glycol (1.0 mL) solution of 0.25 g of tert-butyl 2-(1-benzothiophen-4-yl)-2-cyanoacetate were added 1.0 mL of aqueous solution of 40% (w/w) potassium hydroxide and 0.3 mL of water, which was then stirred at 95 to 105° C. for 1 hour. To the reaction mixture were added water and toluene, and the aqueous layer was separated. The pH was adjusted to 2 with 6 mol/L hydrochloric acid, to which was added ethyl acetate. The organic layer was separated, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. To the resultant residue was added cyclohexane. The precipitate was collected by filtration to provide 0.15 g of 2-(1-benzothiophen-4-yl)acetic acid as white solid form.

Workup

  1. customthe aqueous layer was separated
  2. additionwas added ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. additionTo the resultant residue was added cyclohexane
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-75c57179a1fe48fcb6f71d77ce07b264
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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