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

HRID 1387298Notes

Reaction equation

HRID 1387298 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 acid

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. Tile organic phase was dried, filtered and evaporated to give (4-dimethylaminophenyl)-2,2-dimethylacetic acid as a faint red solid (0.81 0. 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. customTile organic phase was dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-4dc821c86928442195cd19229079c3fe
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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