Reacción #78905

Ecuación de reacción

dimethyl-p-tolyl phosphane

hydrogen peroxide

→

1-(Dimethyl-phosphinoyl)-4-methyl-benzene

Disolventes

—

ice water

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroan exothermic reaction so the flask
2. 2
   workup.ADDITIONAfter the addition the reaction
3. 3
   Otrono starting material (18 h)
4. 4
   OtroFrom the resulting reaction mixture the organic phase
5. 5
   Otrowas separated
6. 6
   Extracciónthe aqueous phase was extracted with additional dichloromethane (3×60 mL) until the aqueous layer
7. 7
   LavadoThe combined organics were washed with a solution of sodium bisulfite (10 mL)
8. 8
   Secadodried over Na2SO4
9. 9
   Concentraciónconcentrated on a rotary evaporator
10. 10
    OtroThe desired product was purified by Crystallization from ethyl acetate/hexane (18.8 g)

Procedimiento

To a solution of dimethyl-p-tolyl phosphane (25 g, 0.165 mol) (1a) in diclholoromethane (DCM) (50 mL) was added an aqueous solution of hydrogen peroxide (10%, 60 mL, 0.176 mol) in drops. This is an exothermic reaction so the flask was cooled in ice water during the addition. After the addition the reaction was allowed to stir at rt overnight until the HPLC showed no starting material (18 h). From the resulting reaction mixture the organic phase was separated and the aqueous phase was extracted with additional dichloromethane (3×60 mL) until the aqueous layer showed little or no evidence of product by HPLC. The combined organics were washed with a solution of sodium bisulfite (10 mL) followed by water (10 mL) and dried over Na2SO4 and concentrated on a rotary evaporator. The desired product was purified by Crystallization from ethyl acetate/hexane (18.8 g). m.p. 90-92° C. 1H NMR (300 MHz, CDCl3) δ (ppm)) 1.469 (d, J=13 Hz, 6H), 2.16 9 (s, 3H), 7.04 (d, J=5.5 Hz, 2H), 7.38 (m, 2H). 31P NMR (121 MHz, CDCl3) δ34.327.

Fuente