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

HRID 491818

반응식

HRID 491818 반응식
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:25]=[O:26])[CH:6]=1

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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 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 followed by 4/1) to give the title compound (1.08 g).

후처리

  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 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: n-hexane/ethyl acetate=9/1 followed by 4/1)

출처 및 근거

ORD 기록
ord-f03f86434a1f4c6c989e07b0698a70bc
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531537B2

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