Hydrochloric Acid → Phenylacetic Acid

HRID 1294313

Reaction equation

HRID 1294313 reaction equation
[C:1]1([CH2:7][C:8]([O-:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.Cl>O1CCCC1CO>[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 4409936Phenylacetate

Product 1

HCID 999Phenylacetic Acid

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

To a solution of methyl 3-[2-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-4-pyridyl]methoxy]phenylacetate (521 mg) in tetrahydrofuran-methanol (1:1, 12 mL) was dropwise added a 1N aqueous sodium hydroxide solution (3 mL) at room temperature, and the mixture was stirred for 1 hr. The reaction mixture was poured into water, and the reaction mixture was neutralized with 1N hydrochloric acid (3 mL) and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals of 3-[2-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-4-pyridyl]methoxy]phenylacetic acid. Recrystallization from ethanol-hexane gave colorless needle crystals (473 mg, 94%). melting point: 136-137° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a9d7ab6c0ff4601a6ce41c734269c5d
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Linked notes

Loading…