Potassium Hydroxide → 2-(2,5-Dimethylphenyl)-2-hydroxyacetic acid

HRID 862187Notes

Reaction equation

HRID 862187 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([OH:20])(C(OCC)=O)[C:10]([O:12]CC)=[O:11].[OH-].[K+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]([OH:20])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12836549Diethyl 2-(2,5-dimethylphenyl)-2-hydroxymalonate

Product 1

HCID 2776622-(2,5-Dimethylphenyl)-2-hydroxyacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of the diethyl (2,5-dimethylphenyl)-hydroxymalonate (21 parts) was reacted with a solution of potassium hydroxide (21 parts) in water (84 parts) at 98° C. for 5 hours. After cooling to ambient temperature, the reaction was washed with diethyl ether and acidified with 10M hydrochloric acid. After heating to 98° C. for a further 2 hours, the cooled materials was extracted into diethyl ether. The separated organic phase was dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude amber coloured oil (15 parts) solidified on standing. Recrystallisation from toluene gave 2,5-dimethylmandelic acid (7 parts). The 1Hnmr, 13Cnmr and mass spectra were all consistent with the structure.

Workup

  1. washthe reaction was washed with diethyl ether
  2. temperatureAfter heating to 98° C. for a further 2 hours
  3. extractionthe cooled materials was extracted into diethyl ether
  4. dry with materialThe separated organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-99c38457053b4093846e6cd5f156bc32
Source dataset
uspto-grants-1998_02
Patent number
US05717112

Reaction notes

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