Potassium Hydroxide → 5-Methoxy-4,4-dimethyl-5-oxopentanoic acid

HRID 217230Notes

Reaction equation

HRID 217230 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][C:7]([O:9]C)=[O:8].[OH-].[K+]>CO>[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:11])([CH3:12])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 830831,5-Dimethyl 2,2-dimethylpentanedioate

Product 1

HCID 134932415-Methoxy-4,4-dimethyl-5-oxopentanoic acidYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-pentanedioic acid dimethyl ester (2.40 g, 12.8 mmol) in MeOH (15 ml) is added potassium hydroxide (0.788 g, 14.0 mmol). The mixture is stirred at room temperature for 16 hours and refluxed for 2 hours. The mixture is cooled to room temperature and concentrated under reduced pressure. To the obtained residue, 1M aqueous HCl (14 ml) is added and the solution is extracted with ether. The organic layer is washed with H2O, dried over Na2SO4, and concentrated under reduced pressure to give 2,2-dimethyl-pentanedioic acid 1-methyl ester (1.97 g, 88%); 1H NMR (400 MHz, chloroform-d) ppm 1.20 (s, 6H), 1.87-1.91 (m, 2H), 2.32-2.36 (m, 2H), 3.67 (s, 3H).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe mixture is cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the obtained residue, 1M aqueous HCl (14 ml) is added
  5. extractionthe solution is extracted with ether
  6. washThe organic layer is washed with H2O
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4249f15011c948e09f097d657c5b0ae0
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

Loading…