Hexamethylenetetramine → 4-Chloro-2-hydroxy-5-methoxybenzaldehyde

HRID 493200Notes

Reaction equation

HRID 493200 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:23](O)=[O:24]>>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:23]=[O:24])=[C:4]([OH:10])[CH:3]=1

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 130819293-Chloro-4-methoxyphenol

Product 1

HCID 107976594-Chloro-2-hydroxy-5-methoxybenzaldehyde

Conditions

Temperature
85 °C

Procedure

The above prepared 3-chloro-4-methoxy-phenol (2.379 g, 13.5 mmol, corrected for purity) was dissolved in 21 mL of trifluoroacetic acid and treated with hexamethylene tetramine (2.313 g, 1.25 eq.), and the mixture was then stirred at 85° C. over night. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, heptane/AcOiPr=82/18), followed by crystallization from heptane/AcOEt, produced finally 1.030 g of the title compound as yellow crystals.

Workup

  1. temperatureCooling
  2. additionpouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. customfollowed by crystallization from heptane/AcOEt

Sources & evidence

ORD record
ord-1ffd0d4c33f04943a563427803df392c
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

Loading…