Reacción #41822

Ecuación de reacción

(chloromethylene)dimethylammonium chloride

4-carboxybenzaldehyde

→

4-Formyl-benzoyl chloride

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat room temperature for 2 h
2. 2
   OtroHPLC analysis of an aliquot of the reaction mixture quenched into MeOH
3. 3
   Otroconsumption of 4-carboxybenzaldehyde
4. 4
   FiltraciónThe reaction mixture was filtered through a medium porosity glass frit
5. 5
   workup.ADDITIONThe filtrate, containing the title compound
6. 6
   Otrowas stored at 0° C.

Procedimiento

A suspension of (chloromethylene)dimethylammonium chloride (Vilsmeier Reagent; 37.7 g, 0.280 mol) in CH2Cl2 (300 mL) at 0° C. was treated with 4-carboxybenzaldehyde (40.0 g, 267 mmol) in one portion. The reaction mixture was stirred at 0° C. for 30 min, then at room temperature for 2 h. HPLC analysis of an aliquot of the reaction mixture quenched into MeOH indicated consumption of 4-carboxybenzaldehyde. The reaction mixture was filtered through a medium porosity glass frit. The filtrate, containing the title compound, was stored at 0° C., and used in the next step without further manipulation.

Fuente