Water → 2-(Thiophen-2-yl)propanoic acid

HRID 1856484Notes

Reaction equation

HRID 1856484 reaction equation
[OH-:1].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([CH:11](Cl)Cl)(O)[CH3:9].[OH2:14]>C1C=CC=CC=1>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]([CH3:9])[C:11]([OH:14])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23345447HCID 23345447, compound

Product 1

HCID 30169222-(Thiophen-2-yl)propanoic acidYield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 40 ml of benzene, 3.93 g of sodium hydroxide (98 mmol) was crushed finely. Under vigorous agitation, 2.09 g of 1-(2-thienyl)-1-dichloromethylethanol (9.9 mmol) was added thereto and agitated for 24 hours at room temperature and then 20 ml of water was added thereto under ice cooling. After washing the diethylether, the aqueous alkaline solution was neutralized (about pH 2) with 6 N hydrochloric acid and extracted with diethylether. The ether layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate and then the ether was distilled off. Thus, 1.22 g of α-(2-thienyl)propionic acid was obtained (yield 79%).

Workup

  1. washAfter washing the diethylether
  2. extractionextracted with diethylether
  3. washThe ether layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe ether was distilled off

Sources & evidence

ORD record
ord-046fdd0d32934ab4ba76168893e43783
Source dataset
uspto-grants-1980_08
Patent number
US04219659

Reaction notes

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