Ethanol → 4-Methoxyphenoxyacetic acid

HRID 1777103Notes

Reaction equation

HRID 1777103 reaction equation
C[C:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].C[CH2:19][OH:20]>>[CH3:19][O:20][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:2][C:3]([OH:5])=[O:4])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86476Deschloroclofibrate

Product 1

HCID 746494-Methoxyphenoxyacetic acid

Procedure

To a solution of ethyl 2-methyl-2-phenoxypropanoate (210 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 before the addition of water (20 mL) and washing with ethyl acetate (2×20 mL). The aqueous layer was acidified with 2N HCL until pH 3 and extracted with ethyl acetate (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 before the addition of water (20 mL)
  2. washwashing with ethyl acetate (2×20 mL)
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9a7ca947280b431db1733e08b0688fd0
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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