Sodium Hydroxide → 2-[2-(Methylsulfonyl)phenoxy]acetic acid

HRID 1777133Notes

Reaction equation

HRID 1777133 reaction equation
[CH3:1][S:2]([C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[O:7][CH2:8][C:9]([O:11]CC)=[O:10])(=[O:4])=[O:3].[OH-].[Na+]>CCO>[CH3:1][S:2]([C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[O:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86729449Ethyl 2-(2-(methylsulfonyl)phenoxy)acetate

Product 1

HCID 232741362-[2-(Methylsulfonyl)phenoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(2-(methylsulfonyl)phenoxy)acetate (750 mg, 2.9 mmol) in EtOH (15 ml) was added 10% NaOH aqueous solution (15 mL) at 26° C. The mixture was stirred for 30 min and then concentrated and the residue diluted with water (20 mL) and washed with ethyl acetate (2×20 mL). The aqueous layer was then acidified with 2N HCL until pH 3 and then 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 diluted with water (20 mL)
  3. washwashed with 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-d08681aa5c65423f8d4dfafcb2d8ae4e
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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