Potassium Hydroxide → 3-Isopropyl-5-methylphenoxyacetic acid

HRID 2182884Notes

Reaction equation

HRID 2182884 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1)([CH3:3])[CH3:2].[Na+].Cl[CH2:14][C:15]([O-:17])=[O:16].[OH-].[K+]>O>[CH:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[O:11][CH2:14][C:15]([OH:17])=[O:16])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 728555-Isopropyl-m-cresolHCID 23665759Sodium chloroacetate

Product 1

HCID 167698883-Isopropyl-5-methylphenoxyacetic acidYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Isopropyl-5-methylphenol (44.0 g, 0.29 mol) and chloroacetic acid sodium salt (35.0 g, 0.3 mol) was dissolved in 180 mL of H2O, and then KOH (86%, 20 g, 0.3 mol) was added slowly. The reaction mixture was refluxed overnight and thereafter concentrated by distillation. After cooling, the mixture was acidified to pH 1, and then extracted with EtOAc. The organic layer was washed H2O, dried over MgSO4, and concentrated. The solid was recrystalized in 5% isopropanol in hexane to give pure 3-isopropyl-5-methylphenoxyacetic acid (38 g, 63%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated by distillation
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe solid was recrystalized in 5% isopropanol in hexane

Sources & evidence

ORD record
ord-fa24f6b04f484bdea16c3f9577b01b11
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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