Sulfuric Acid → 2-Hydroxy-5-tetrazol-2-yl-benzaldehyde

HRID 1941511Notes

Reaction equation

HRID 1941511 reaction equation
C1N2CN3CN(C2)CN1C3.[N:11]1[N:12]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[N:13]=[N:14][CH:15]=1.S(=O)(=O)(O)O.FC(F)(F)[C:30](O)=[O:31]>>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([N:12]2[N:13]=[N:14][CH:15]=[N:11]2)=[CH:21][C:20]=1[CH:30]=[O:31]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 157603994-(2H-Tetrazol-2-yl)phenol

Product 1

HCID 104879002-Hydroxy-5-tetrazol-2-yl-benzaldehyde

Procedure

Hexamethylenetetramine (5.6 g) was added to 4-tetrazol-2-yl-phenol (1.6 g) in trifluoroacetic acid (40 ml) and the mixture heated at 60° for 24 h. On cooling, the solution was poured into sulphuric acid (2N, 100 ml), extracted with ether (3×100 ml), dried (Na2SO4) and evaporated. The residue was purified by FCC (dichloromethane) to give the title compound as a yellow solid (930 mg). T.l.c. (Dichloromethane), Rf 0.56.

Workup

  1. temperaturethe mixture heated at 60° for 24 h
  2. temperatureOn cooling
  3. extractionextracted with ether (3×100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by FCC (dichloromethane)

Sources & evidence

ORD record
ord-85534c24397447ffa60b375b4f63d1db
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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