Acetic Acid → 3,5-Diethyl-4-hydroxybenzaldehyde

HRID 2353619

반응식

HRID 2353619 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[OH:11])[CH3:2].[C:12](O)(=[O:14])C>>[CH2:1]([C:3]1[CH:8]=[C:7]([CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[OH:11])[CH:12]=[O:14])[CH3:2]

참가 물질

3

반응물 2

HCID 176Acetic AcidHCID 705072,6-Diethylphenol

생성물 1

HCID 30179473,5-Diethyl-4-hydroxybenzaldehyde수율 39.9%

반응 조건

온도
120 °C

실험 절차

To a solution of 2,6-diethylphenol (3.80 g, 25.3 mmol) in acetic acid (30 mL) hexamethylenetetraamine (5.3 g, 37.9 mmol) is added and the mixture is heated to 120° C. A first fraction of the solvent is distilled off (Dean-Stark), then the mixture is refluxed for 3 h. The mixture is cooled to rt, diluted with water (100 mL) and extracted twice with EA (2×200 mL). The organic extracts are washed with sat. aq. NaHCO3, dried and the solvent is removed in vacuo. The crude product is purified by column chromatography eluting with DCM containing 2% of methanol to give 3,5-diethyl-4-hydroxybenzaldehyde (1.8 g) as colourless solid; 1H NMR (CDCl3): δ 9.85 (s, 1H), 7.57 (s, 2H), 5.32 (s, 1H), 2.69 (q, J=7.6 Hz, 2H), 1.30 (t, J=7.6 Hz, 3H).

후처리

  1. distillationA first fraction of the solvent is distilled off (Dean-Stark)
  2. temperaturethe mixture is refluxed for 3 h
  3. temperatureThe mixture is cooled to rt
  4. additiondiluted with water (100 mL)
  5. extractionextracted twice with EA (2×200 mL)
  6. washThe organic extracts are washed with sat. aq. NaHCO3
  7. customdried
  8. customthe solvent is removed in vacuo
  9. customThe crude product is purified by column chromatography
  10. washeluting with DCM containing 2% of methanol

출처 및 근거

ORD 기록
ord-d44afbe7a2ec49a2a9f3678c866a74c6
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750040B2

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