تفاعل #95204

معادلة التفاعل

4,4'-bis(N,N-dimethylamino)benzhydrol

methyl ether

ethyl glycolate

tetrahydrofuran

→

Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Ethyl Ester

المذيبات

n-hexane

—

petroleum ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   ترشيحThe reaction mixture was filtered hot
3. 3
   درجة الحرارةthe filtrate was cooled
4. 4
   أخرىAn oily layer formed which
5. 5
   أخرىwas removed
6. 6
   أخرىleaving an oil
7. 7
   درجة الحرارةchilled
8. 8
   أخرىA waxy solid formed which
9. 9
   أخرىgave a white solid
10. 10
    أخرىRecrystallization
11. 11
    workup.ADDITIONfrom a mixture of petroleum ether/acetone
12. 12
    أخرىgave a white solid, mp 63°-67.5° C.

الإجراء التجريبي

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (11.0 g, 0.039 mole), ethyl glycolate 4.04 g, 0.039 mole), 70 ml of tetrahydrofuran, 230 ml of n-hexane and one drop of methanesulfonic acid was refluxed for 2 hours. On completion of the reaction, 2 drops of tetramethylguanidine was added to discharge the blue color. The reaction mixture was filtered hot and the filtrate was cooled. An oily layer formed which was removed and stripped free of solvent; the remaining filtrate was also stripped, leaving an oil. Both samples of oil were combined and chilled. A waxy solid formed which, on repeated trituration with petroleum ether, gave a white solid. Recrystallization from a mixture of petroleum ether/acetone gave a white solid, mp 63°-67.5° C.

المصدر