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

HRID 2164129Notes

Reaction equation

HRID 2164129 reaction equation
CS[CH:3]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:4]([O:6]C)=[O:5].[OH-].[K+].O.S(=O)(=O)(O)O.[CH3:21]OCCOC>>[CH3:21][CH:3]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 80711,2-DimethoxyethaneHCID 14797Potassium HydroxideHCID 12327263HCID 12327263, compound

Product 1

HCID 30169222-(Thiophen-2-yl)propanoic acid

Procedure

Methyl α-methylthio(2-thienyl)acetate (1.956 g) was dissolved in 20 ml of 1,2-dimethoxyethane, and 10 ml of a 2N aqueous solution of potassium hydroxide was added. The mixture was stirred at room temperature for 2 hours and 50 minutes. Water (20 ml) and 10 ml of 3N sulfuric acid were added. The mixture was extracted four times with 50 ml of diethyl ether. The ethereal layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 1.668 g of α-methyl(2-thienyl)acetic acid as pale yellow crystals. Recrystallization from diethyl ether/n-hexane afforded crystals having a melting point of 75 to 75.5° C.

Workup

  1. extractionThe mixture was extracted four times with 50 ml of diethyl ether
  2. dry with materialThe ethereal layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-694864a693374f0e83b2defa87ab1e68
Source dataset
uspto-grants-1979_01
Patent number
US04137406

Reaction notes

Loading…