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

HRID 2353619

反応式

HRID 2353619 の反応式
[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]

参加物

3

反応物 2

HCID 176Acetic AcidHCID 705072,6-Diethylphenol

生成物 1

HCID 30179473,5-Diethyl-4-hydroxybenzaldehyde収率 39.9%

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d44afbe7a2ec49a2a9f3678c866a74c6
出典データセット
uspto-grants-2010_07
特許番号
US07750040B2

関連ノート

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