Sodium Hydroxide → 4-Isopropylphenoxyacetic acid

HRID 1269501Notes

Reaction equation

HRID 1269501 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:16])=[O:3])=[CH:8][CH:9]=1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10822915Ethyl-(4-isopropylphenoxy)acetate

Product 1

HCID 1371314-Isopropylphenoxyacetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl-(4-isopropylphenoxy)acetate (1.61 g, 7.24 mmol) and 2N NaOH(aq) (10.9 mL) in 20 mL of methanol was stirred at ambient temperature for 3 h and concentrated under reduced pressure. The resulting residue was taken up in water (100 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2×100 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 1.32 g (94%) of 4-isopropylphenoxyacetic acid as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09dbe736ef874da198be2f293a99aa07
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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