Reacción #66042

Ecuación de reacción

4-hydroxyphenylacetaldehyde

Pyridine-sulfur trioxide

3-(4-Hydroxyphenyl)-1-propanol

→

4-hydroxyphenylpropionaldehyde

Rendimiento 75.0%

Disolventes

CH2Cl2

dimethylsulfoxide

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 1 h at room temperature
2. 2
   Lavadowashed with ice-cold water
3. 3
   SecadoThe organic layer was dried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated to dryness
6. 6
   OtroPurification

Procedimiento

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.

Fuente