Hydrogen Peroxide → Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl ester

HRID 2308829Notes

Reaction equation

HRID 2308829 reaction equation
OO.[CH3:3]C(C1C=CC(OC(C)C(O)=O)=CC=1)=C.[OH:18][C:19]1[CH:30]=[CH:29][C:22]([O:23][CH:24]([CH3:28])[C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1>CO>[OH:18][C:19]1[CH:20]=[CH:21][C:22]([O:23][CH:24]([CH3:28])[C:25]([O:27][CH3:3])=[O:26])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1011822-(4-Hydroxy-phenoxy)-propionic acidHCID 20187936HCID 20187936, compound

Product 1

HCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen peroxide (67% H2O2, 0.60 equivalents) was added to a mixture of 0.005 equivalents of Dowex® MSC-1 sulfonic acid resin in the proton form, 0.050 equivalents 2-(4-(1-methylethenyl)phenoxy)propanoic acid (prepared by base hydrolysis of methyl 2-(4-(1-methylethenyl)phenoxy)propanoate), and 11 ml methanol at room temperature. The mixture was refluxed about 10 hours. (The oxidation was complete after about 1.5 hour, but about 10 hours were required for the simultaneous esterification.) Workup gave 8.3 g of methyl 2-(4-hydroxyphenoxy)propanoate containing a small amount of 2-(4-hydroxyphenoxy)propanoic acid.

Workup

  1. temperatureThe mixture was refluxed about 10 hours
  2. customabout 10 hours

Sources & evidence

ORD record
ord-33d37e0c5ca94c6fbd7df71d1e7e84f8
Source dataset
uspto-grants-1987_09
Patent number
US04691042

Reaction notes

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