Acetic Acid → 2-(4-Acetamidophenoxy)propionic acid

HRID 1639413Notes

Reaction equation

HRID 1639413 reaction equation
C([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)(=O)C.S(O)(O)(=O)=O.[NH2:21]O.C(=O)([O-])[O-].[Na+].[Na+].[C:29]([OH:32])(=O)[CH3:30]>S(=O)(=O)(O)O.O>[C:29]([NH:21][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)(=[O:32])[CH3:30]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 159255Hydroxylamine, sulfate (1:1)HCID 51606492-(4-acetylphenoxy)propanoic Acid

Product 1

HCID 167904892-(4-Acetamidophenoxy)propionic acidYield 95%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A solution of 2-(4-acetylphenoxy)propionic acid (1.5 g, 7.2 mmol), hydroxylamine sulfate (0.72 g, 4.4 mmol), and concentrated sulfuric acid (2 drops) in acetic acid (30 mL) is refluxed for 4.25 hours. The reaction is quenched with sodium carbonate (0.25 g, 2.4 mmol) and concentrated to give a residue. The reaction residue is dissolved in water (50 mL) and extracted with ethyl acetate (2×100 mL). The ethyl acetate extract is dried and concentrated to give 2-(4-acetamidophenoxy)propionic acid (1.53 g) (yield 95%): m.p. 170°-172° C.; IR (KBr) 3400 (vs), 2900 (s) 1730 (vs), 1630 (vs), and 1603 (vs); 1H NMR (DMSO-d6) delta 1.47 (d, J=6.8 Hz, 3H), 1.87 (s,3H), 2.06 (s,3H), 4.65 (q, J=6.8 Hz, 1H), 6.73 and 7.42 (dd, J=9.0 Hz, 4H).

Workup

  1. concentrationconcentrated
  2. customto give a residue
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. extractionThe ethyl acetate extract
  5. customis dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-66d10c86d8304d8b80651ce8c0cc7eb6
Source dataset
uspto-grants-1989_11
Patent number
US04883901

Reaction notes

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