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

HRID 2308827Notes

Reaction equation

CC([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)=C.OO.[OH:19]S(O)(=O)=O.[O-]S([O-])=O.[Na+].[Na+]>C(O)(=O)C.O>[OH:19][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

Participants

Conditions

Temperature: 10 °C

Procedure

An 86.0 g-portion of methyl 2-(4-(1-methylethenyl)phenoxy)propanoate was dissolved in 360 ml glacial acetic acid. An equimolar portion of 30% aqueous H2O2 was added. The solution was cooled to 10° C. and 7.6 mol% of 98% H2SO4 was added. The solution was allowed to slowly warm to 35° C. over 11 minutes at which point the ice bath was put back on. The temperature peaked at 84° C. two minutes later. The reaction mixture was allowed to cool slowly to 36° C. over 25 minutes. A 26 g-portion of 20% aqueous Na2SO3 was added, followed by 900 ml water. The mixture was extracted with four 200 ml-portions of CH2Cl2. The combined organic layers were washed with two 200 ml-portions and one 400 ml-portion of 5% aqueous NaHCO3. The organic layer was dried with Na2SO4. Removal of solvent gave 74.8 of 94% pure methyl 2-(4-hydroxyphenoxy)propanoate, corresponding to a 92% yield. Distillation under reduced pressure gave 59.3 g of methyl 2-(4-hydroxyphenoxy)propanoate (b.p. 154°-155° C./4 torr) corresponding to a 77% yield.

Workup

temperatureto cool slowly to 36° C. over 25 minutes
extractionThe mixture was extracted with four 200 ml-portions of CH2Cl2
washThe combined organic layers were washed with two 200 ml-portions and one 400 ml-portion of 5% aqueous NaHCO3
dry with materialThe organic layer was dried with Na2SO4
customRemoval of solvent

Sources & evidence

ORD record: ord-5dbdb47020504a588260fdf21818f7d1
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04691042

Reaction notes

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