Reaktion #95208

Reaktionsgleichung

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

methyl ether

benzyl glycolate

tetrahydrofuran

→

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

Lösungsmittel

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed
2. 2
   workup.ADDITIONthen, 10 drops of tetramethylguanidine was added
3. 3
   Filtrationthe reaction mixture was filtered hot
4. 4
   Temperaturcooled
5. 5
   SonstigeA white solid formed which
6. 6
   Filtrationwas filtered
7. 7
   Waschenwashed with petroleum ether
8. 8
   Sonstigerecrystallized from 4/1 hexane/acetone

Vorschrift

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (11.0 g, 0.039 mole), benzyl glycolate (6.6 g, 0.039 mole), 90 ml of tetrahydrofuran, 200 ml of hexane, and 10 drops of methanesulfonic acid was refluxed for 6 hours, replacing solvent as distillate was removed; then, 10 drops of tetramethylguanidine was added to discharge the color and the reaction mixture was filtered hot and cooled. A white solid formed which was filtered, washed with petroleum ether and then recrystallized from 4/1 hexane/acetone. The resulting white crystalline product had a mp 101.8°-103° C.

Quelle