3-(4-Hydroxyphenyl)propanol → 2-(4-Hydroxyphenyl)propanal

HRID 37764

反応式

HRID 37764 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[O:10])=[CH:4][CH:3]=1.O[C:12]1C=CC(CCCO)=CC=1.C1C=CN=CC=1.O=S(=O)=O>CS(C)=O.C(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[CH:9]=[O:10])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 824523-(4-Hydroxyphenyl)propanolHCID 168533Sulfur trioxide-pyridineHCID 4401134-Hydroxyphenylacetaldehyde

生成物 1

HCID 132271832-(4-Hydroxyphenyl)propanal収率 75%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

4-hydroxyphenylpropionaldehyde was prepared by a synthesis analogous to that for 4-hydroxyphenylacetaldehyde (Heterocycles, 2000, 53, 777-784). 3-(4-Hydroxyphenyl)-1-propanol (1.0 g, 6.6 mmol, Aldrich) was dissolved in dimethylsulfoxide (8 mL, Aldrich). TEA (2.0 mL, 14 mmol, Aldrich) was added slowly with stirring. Pyridine-sulfur trioxide (SO3.py) complex (2.3 g, 15 mmol, Aldrich) was completely dissolved in dimethylsulfoxide (9 mL, Aldrich) and this solution was added drop-wise to the alcohol, with vigorous stirring. After stirring for 1 h at room temperature, the reaction was diluted with CH2Cl2, then washed with ice-cold water. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness. Purification using silica gel chromatography with hexane-ethyl acetate as eluent (5:1, then 2:1) yielded 745 mg (75%) of 4-hydroxyphenylpropionaldehyde.

後処理

  1. stirringAfter stirring for 1 h at room temperature
  2. washwashed with ice-cold water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customPurification

出典と根拠

ORDレコード
ord-a7aacc3f8cea49a0a46cccab84016b4e
出典データセット
uspto-grants-2013_09
特許番号
US08524660B2

関連ノート

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