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

HRID 1589118Notes

Reaction equation

HRID 1589118 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-0b8630440b4945f3b733d20996af8c79
Source dataset
uspto-grants-1986_02
Patent number
US04568497

Reaction notes

Loading…