Hexamethylenetetramine → 2-Hydroxy-5-(5-trifluoromethyl-tetrazol-1-yl)benzaldehyde

HRID 376271Notes

Reaction equation

HRID 376271 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[N:6]=[N:5][N:4]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:29](O)=[O:30]>>[OH:14][C:11]1[CH:10]=[CH:9][C:8]([N:7]2[C:3]([C:2]([F:1])([F:15])[F:16])=[N:4][N:5]=[N:6]2)=[CH:13][C:12]=1[CH:29]=[O:30]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 211972494-(5-Trifluoromethyl-tetrazol-1-YL)-phenol

Product 1

HCID 112769072-Hydroxy-5-(5-trifluoromethyl-tetrazol-1-yl)benzaldehyde

Procedure

A solution of 4-(5-trifluoromethyl-tetrazol-1-yl)-phenol (45 mmol) in trifluoroacetic acid (200 ml) and hexamethylenetetramine (186.9 mmol) was heated at 100° under nitrogen for 16 h. The reaction mixture was quenched with 2N sulphuric acid (250 ml) and extracted with ether (3×250 ml)). The combined organics were dried (Na2SO4) and evaporated to give a dark yellow oil. Purification by FCC (hexane/ether (2:1)) afforded the title compound (8.8 g) as a pale yellow solid.

Workup

  1. customThe reaction mixture was quenched with 2N sulphuric acid (250 ml)
  2. extractionextracted with ether (3×250 ml))
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. customevaporated
  5. customto give a dark yellow oil
  6. customPurification by FCC (hexane/ether (2:1))

Sources & evidence

ORD record
ord-6ed914aae22f4d22951d8ded0091096c
Source dataset
uspto-grants-2000_02
Patent number
US06020346

Reaction notes

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