Réaction #66041

Équation de réaction

Pyridine-sulfur trioxide

4-Hydroxyphenethyl alcohol

→

4-hydroxyphenylacetaldehyde

Rendement 49.1%

Solvants

dimethylsulfoxide

—

Heterocycles

dimethylsulfoxide

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Autre4-hydroxyphenylacetaldehyde (15) was synthesized
2. 2
   workup.STIRRINGAfter stirring for 1 h at room temperature
3. 3
   Lavagewashed with ice-cold water
4. 4
   SéchageThe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated to dryness
7. 7
   AutrePurification

Mode opératoire

4-hydroxyphenylacetaldehyde (15) was synthesized as described in Heterocycles, 2000, 53, 777-784. 4-Hydroxyphenethyl alcohol (Compound 141.0 g, 7.3 mmol, Aldrich) was dissolved in dimethylsulfoxide (8 mL, Aldrich). With stirring, TEA (2.2 mL, 16 mmol, Aldrich) was added slowly. Pyridine-sulfur trioxide (SO3.py) complex (2.5 g, 16 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 488 mg (49%) of 4-hydroxyphenylacetaldehyde (15).

Source