Water → 2-Methyl-2-(thiophen-2-yl)propanoic acid

HRID 1940433Notes

Reaction equation

HRID 1940433 reaction equation
[CH3:1][C:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([CH3:7])[C:3]([O:5]C)=[O:4].[OH-].[K+].O>O1CCOCC1>[CH3:7][C:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11423980Methyl 2-Methyl-2-(2-thienyl)propanoate

Product 1

HCID 190849342-Methyl-2-(thiophen-2-yl)propanoic acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution containing 17.5 g of methyl 2-methyl-2-(2-thienyl)propionate [prepared as described in step (i) above], 12.6 g of potassium hydroxide, 72 ml of water, and 168 ml of 1,4-dioxane was heated under reflux for 2 hours. At the end of this time, it was diluted with ice-water, and extracted twice with diethyl ether. The aqueous layer was adjusted to a weakly acidic pH, extracted three times with diethyl ether, washed with water and with a saturated aqueous solution of sodium chloride, in that order, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure to give 15.8 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted twice with diethyl ether
  4. extractionextracted three times with diethyl ether
  5. washwashed with water and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d733a5a154844610baa967334dc23bd1
Source dataset
uspto-grants-1997_12
Patent number
US05698720

Reaction notes

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