Peracetic Acid → Methyl 2-(4-acetoxyphenoxy)propanoate

HRID 1085332Notes

Reaction equation

HRID 1085332 reaction equation
C([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)(=O)C.[C:17]([O:20]O)(=[O:19])[CH3:18].OC1C=CC(OC(C)C(OC)=O)=CC=1>C(O)(=O)C>[C:17]([O:20][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:15][CH:16]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterHCID 14717334Methyl 2-(4-acetylphenoxy)propanoate

Product 1

HCID 20062087Methyl 2-(4-acetoxyphenoxy)propanoateYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 2-(4-acetylphenoxy)propanoate (5.6g, 25.0 mmol) in acetic acid (25 mL) is added peracetic acid (35%, 6.5g, 30.0 mmol) dropwise over 30 minutes at 25° C. The reaction is refluxed at 70° C. for 5 hours to give an orange-brown liquid. Acetic acid and residual peracetic acid are removed by high vacuum. The solution is kugelrohr distilled to give a light brown-orange product which contains methyl 2-(4-acetoxyphenoxy)propanoate (conversion 93%, selectivity 76%, yield 71%) and methyl 2-(4-hydroxyphenoxy)propanoate.

Workup

  1. customto give an orange-brown liquid
  2. customAcetic acid and residual peracetic acid are removed by high vacuum
  3. distillationThe solution is kugelrohr distilled
  4. customto give a light brown-orange product which

Sources & evidence

ORD record
ord-edfea0a34b65454da9995d06e33b4ba3
Source dataset
uspto-grants-1991_04
Patent number
US05008439

Reaction notes

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