Hexamethylenetetramine → Methyl 2-(3-formyl-4-hydroxyphenyl)acetate

HRID 1820930Notes

Reaction equation

HRID 1820930 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>>[CH:25]([C:7]1[CH:6]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1])=[O:26]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 12374099Methyl 2-(3-formyl-4-hydroxyphenyl)acetate

Procedure

Methyl (4-hydroxyphenyl)acetate (1.66 g) is dissolved in trifluoroacetic acid (20 ml), thereto is added hexamethylenetetramine (700 mg), and the mixture is heated under reflux for 2 hours. The reaction solution is concentrated under reduced pressure, thereto is poured ice-water, and then the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate =9/1, then 4/1) to give the title compound (1.08 g). ESI-MS M/Z:193[M−H]−

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. additionis poured ice-water
  5. extractionthe mixture is extracted with ethyl acetate
  6. washThe organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto remove the solvent under reduced pressure
  10. customThe resulting residue is purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-a98db4c5db0645bb94d15bc93f5d12f0
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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