Hydrochloric Acid → HCID 22722091, compound

HRID 1581682Notes

Reaction equation

HRID 1581682 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])(=[O:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22722095HCID 22722095, compound

Product 1

HCID 22722091HCID 22722091, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 2-(3-acetamidophenoxy)benzoate (4.7 g crude mixture) in dioxane (100 mL) was added 1.0 N NaOH (24 mL). After stirring at RT for 72 hr the reaction was acidified with 1.0 N HCl (24 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried (Mg SO4), and concentrated. The residue was purified by flash chromatography on silica gel (95:4:1 CHCl3/MeOH/AcOH) to give the crude title compound (2.2 g, 34%) as a beige solid: MS (ES) m/e 272.2 (M+H)+. The title compound prepared in this way contained approximately 46% of the diacid resulting from the di-ester starting material contaminant: MS (ES) m/e 392.2 (M+H)+. The mixture was used without further purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Mg SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (95:4:1 CHCl3/MeOH/AcOH)

Sources & evidence

ORD record
ord-72a9672592a843a3b17ebf54894f6fa6
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Reaction notes

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