Hydrochloric Acid → 2-[4-(Dimethylamino)phenyl]-2-methylpropanoic acid

HRID 1005427Notes

Reaction equation

HRID 1005427 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:16])([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C.O>[CH3:17][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([CH3:15])([CH3:16])[C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57182128HCID 57182128, compound

Product 1

HCID 206960032-[4-(Dimethylamino)phenyl]-2-methylpropanoic acidYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl (4-dimethylaminophenyl)-2,2-dimethylacetate (1.00 g, 4.25 mmol) and sodium hydroxide (0.85 g) in ethanol (20 ml ) and water (9 mL) was heated under reflux for 18 hours. The mixture was cooled, acidified with 10% HCl, and washed with ethyl acetate. The aqueous phase was evaporated. The residue was dissolved in aqueous saturated sodium bicarbonate, and extracted with ethyl acetate. The organic phase was dried, filtered and evaporated to give (4-dimethylaminophenyl)-2,2-dimethylacetic acid as a faint red solid (0.81 g, 92%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. washwashed with ethyl acetate
  5. customThe aqueous phase was evaporated
  6. dissolutionThe residue was dissolved in aqueous saturated sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. customThe organic phase was dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-ae6e576aba264cbd81bac924c02d5987
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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