Peracetic Acid → 2-(4-Acetoxyphenoxy)propanoic acid

HRID 1165346Notes

Reaction equation

HRID 1165346 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.[C:16]([O:19]O)(=[O:18])[CH3:17]>C(O)(=O)C>[C:16]([O:19][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:18])[CH3:17]

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 51606492-(4-acetylphenoxy)propanoic Acid

Product 1

HCID 147448922-(4-Acetoxyphenoxy)propanoic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(4-acetylphenoxy)propanoic acid (5.08 g, 24.4 mmol) in acetic acid (20 mL) is added purified peracetic acid (16%, 15.80 g, 33.3 mmol) over 30 minutes. The reaction mixture is stirred under reflux at 55° C. to 60° C. and 60-64 mm Hg for 9 hours. The solution is rotovapped and vacuumed to remove the acetic acid. The product obtained is 5.0 g of 2-(4-acetoxyphenoxy)propanoic acid (yield 91%): m.p. 102° C., 1H NMR (CDCl3, delta 1.63 (d, J=7.0 Hz, 3H), 2.26 (s, 3H), 4.85 (q, J=7.0 Hz, 1H), 7.10 (m, 4H).

Workup

  1. temperatureunder reflux at 55° C. to 60° C.
  2. customto remove the acetic acid
  3. customThe product obtained

Sources & evidence

ORD record
ord-49b392ad47f943cda6952401cff993f5
Source dataset
uspto-grants-1990_03
Patent number
US04908476

Reaction notes

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