Reaction #362821

Reaction equation

hexadecanol

N-methylimidazole

p-Nitrophenyl phosphorodichloridate

→

n-hexyl p-nitrophenyl phosphorochloridate

Solvents

dichloromethane

hexane

dichloromethane

Conditions

Workup

1. 1
   Otherhad been purged with N2
2. 2
   workup.STIRRINGThe reaction mixture was stirred for an additional 1 hour
3. 3
   workup.ADDITIONbefore pouring into a 1 L separatory funnel
4. 4
   OtherN-methylimidazole hydrochloride salts separated at the bottom as an oil
5. 5
   Otherwere removed from the funnel
6. 6
   OtherDichloromethane was removed from the mixture at less than 30° C. under vacuum
7. 7
   Otherto give an amber oil which
8. 8
   Filtrationthe soluble portion was filtered
9. 9
   Otherto remove the crystals of p-nitrophenyl phosphorodichloridate
10. 10
    OtherThe solvent was removed from the filtrate via rotary evaporation at less than 35° C.

Procedure

p-Nitrophenyl phosphorodichloridate (75 g, 0.29 mol) in anhydrous dichloromethane (300 mL) was added to a 1 L, three necked, round-bottomed flask with stir bar that had been purged with N2. A solution of hexadecanol (71.03 g, 0.29 mol) and N-methylimidazole (23.35 mL, 0.29 mol) in anhydrous dichloromethane (250 mL) was added dropwise over a period of 2 hours. The reaction mixture was stirred for an additional 1 hour before pouring into a 1 L separatory funnel. N-methylimidazole hydrochloride salts separated at the bottom as an oil and were removed from the funnel. Dichloromethane was removed from the mixture at less than 30° C. under vacuum to give an amber oil which was taken up in hexane (400 mL) and placed in a freezer overnight. The reaction mixture was then thawed and the soluble portion was filtered to remove the crystals of p-nitrophenyl phosphorodichloridate. The solvent was removed from the filtrate via rotary evaporation at less than 35° C. to give n-hexyl p-nitrophenyl phosphorochloridate.

Source