Sodium Hydroxide → p-Methylphenoxyacetic acid

HRID 1429431Notes

Reaction equation

HRID 1429431 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([O:11]CC)=[O:10])=[CH:3][CH:2]=1.[OH-].[Na+]>CCO>[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4047281Ethyl (p-tolyloxy)acetate

Product 1

HCID 70329p-Methylphenoxyacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(p-tolyloxy)acetate (200 mg, 1 mmol) in EtOH (10 ml) was added 10% NaOH solution (10 ml) at 26° C. The mixture was stirred for 30 min, concentrated then water (20 mL) added to it before washing with ethyl acetate (2×20 mL). The aqueous layer was acidified with 2N HCL until pH 3 and extracted with EA (2×20 ml). The organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification.

Workup

  1. concentrationconcentrated
  2. additionwater (20 mL) added to it
  3. washbefore washing with ethyl acetate (2×20 mL)
  4. extractionextracted with EA (2×20 ml)
  5. washThe organic layer was washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a411d46768aa47ae8ce8228d2a2c1153
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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