Potassium Hydroxide → 2-Methyl-2-(oxan-4-yl)propanoic acid

HRID 252374Notes

Reaction equation

HRID 252374 reaction equation
C([O:3][C:4](=[O:14])[C:5]([CH3:13])([CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[CH3:6])C.[OH-].[K+]>C(O)C>[CH3:13][C:5]([CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1)([CH3:6])[C:4]([OH:14])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57429863HCID 57429863, compound

Product 1

HCID 668885952-Methyl-2-(oxan-4-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.795 g of 2-methyl-2-(tetrahydro-pyran-4-yl)-propionic acid ethyl ester in 3 ml of ethanol is admixed with 3 ml of a 40% aqueous potassium hydroxide solution and then heated to reflux. After 4 hours, the reaction mixture is cooled to room temperature and the ethanol removed in vacuo. The remaining aqueous solution is acidified (pH 2-3) with 4M HCl and then extracted with tert-butyl methyl ether (2×). The combined organic layers are washed with water and brine, dried over sodium sulphate and concentrated by evaporation to provide the crude title compound as a yellow solid. Rf=0.10 (1:3 EtOAc-heptane).

Workup

  1. temperatureheated to reflux
  2. customthe ethanol removed in vacuo
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2fd9a7ed3e7c48a596db03d726716639
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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