Réaction #1868992

ord-5756335bac1345b98f6e307f0bc24576

Équation de réaction

COc1cc(C=O)cc(C=O)c1O
4-hydroxy-5-methoxy-isophthalaldehyde
Br
hydrobromic acid
O=Cc1cc(O)c(O)c(C=O)c1
4,5-dihydroxyisophthalaldehyde

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureheated
  2. 2
    Températureunder reflux
  3. 3
    workup.ADDITIONare added
  4. 4
    Filtrationthe separated precipitate is filtered under suction
  5. 5
    Lavagewashed with water
  6. 6
    Filtrationfiltered ever 50 g of aluminum oxide (activity grade II)
  7. 7
    AutreThe crystalline material obtained
  8. 8
    Autreis recrystallized from ethyl acetate/n-hexane

Mode opératoire

5.0 g of 4-hydroxy-5-methoxy-isophthalaldehyde are treated with 50 ml of constant-boiling hydrobromic acid and heated to boiling under reflux and while stirring under an argon atmosphere for 3 hours. After cooling 50 ml of ice-water are added thereto, and the separated precipitate is filtered under suction and washed with water. The crude product is taken up in ethyl acetate and filtered ever 50 g of aluminum oxide (activity grade II). The crystalline material obtained is recrystallized from ethyl acetate/n-hexane. There is obtained 4,5-dihydroxyisophthalaldehyde in the form of slightly, orange crystals of m.p. 201°-202°.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05633371uspto-grants-1997_05