Sodium Hydroxide → 4-Acetaminophenoxyacetic acid

HRID 1777112Notes

Reaction equation

HRID 1777112 reaction equation
[C:1]([NH:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13]CC)=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([NH:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 309738Ethyl 2-(4-acetamidophenoxy)acetate

Product 1

HCID 1014374-Acetaminophenoxyacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(4-acetamidophenoxy)acetate (237 mg, 1 mmol) in EtOH (10 ml) was added 10% NaOH aqueous solution (10 mL) at 26° C. The mixture was stirred for 30 min and then concentrated. The residue was diluted with water (20 mL) and washed ethyl acetate (2×20 mL). The aqueous layer was then acidified with 2N HCL until pH 3 and extracted with ethyl acetate (2×20 ml). The combined organic layers were 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. additionThe residue was diluted with water (20 mL)
  3. washwashed ethyl acetate (2×20 mL)
  4. extractionextracted with ethyl acetate (2×20 ml)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1d5135ab293c45f5950facbf53a63a16
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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