Reaction #95204

Reaction equation

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

methyl ether

ethyl glycolate

tetrahydrofuran

→

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

Solvents

n-hexane

—

petroleum ether

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   FiltrationThe reaction mixture was filtered hot
3. 3
   Temperaturethe filtrate was cooled
4. 4
   OtherAn oily layer formed which
5. 5
   Otherwas removed
6. 6
   Otherleaving an oil
7. 7
   Temperaturechilled
8. 8
   OtherA waxy solid formed which
9. 9
   Othergave a white solid
10. 10
    OtherRecrystallization
11. 11
    workup.ADDITIONfrom a mixture of petroleum ether/acetone
12. 12
    Othergave a white solid, mp 63°-67.5° C.

Procedure

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.

Source