Hydrochloric Acid → (2-isopropylphenoxy)acetic acid

HRID 369873Notes

Reaction equation

HRID 369873 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21]CC)=[O:20].Cl>CN(C)C=O.[OH-].[Na+].O.C(O)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:18][C:19]([OH:21])=[O:20])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 69432-IsopropylphenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 1284361(2-isopropylphenoxy)acetic acid

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of o-isopropylphenol (39.5 g), potassium carbonate (40 g) and ethyl α-bromoacetate (40 ml) in dimethylformamide (300 ml) is heated with stirring at 80° C. for 8 hours. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated under reduced pressure to remove the solvent. The residue thus obtained is dissolved in a solution of sodium hydroxide (20 g) in water (300 ml) and ethanol (200 ml), and the mixture is refluxed for 1.5 hour. After cooling, the mixture is acidified with conc. hydrochloric acid, and the precipitated crystals are collected by filtration to give α-(2-isopropylphenoxy)acetic acid (37 g).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto remove the solvent
  6. customThe residue thus obtained
  7. temperaturethe mixture is refluxed for 1.5 hour
  8. temperatureAfter cooling
  9. filtrationthe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-c4d8965321b840eea16f4e1123d89cd1
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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