تفاعل #1676298

معادلة التفاعل

H2SO4

Na2SO3

methyl 2-(4-(1-methylethenyl)phenoxy)propanoate

H2O2

→

methyl 2-(4-hydroxyphenoxy)propanoate

المردود 94.0%

المذيبات

acetic acid

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool slowly to 36° C. over 25 minutes
2. 2
   استخلاصThe mixture was extracted with four 200 ml-portions of CH2Cl2
3. 3
   غسيلThe combined organic layers were washed with two 200 ml-portions and one 400 ml-portion of 5% aqueous NaHCO3
4. 4
   تجفيفThe organic layer was dried with Na 2 SO4
5. 5
   أخرىRemoval of solvent

الإجراء التجريبي

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 Na 2 SO4. 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.

المصدر