Hydrogen Peroxide → ((11-Hydroxyundecyl)-ethoxyphosphinyl)methylphosphonic acid dimethyl ester

Participants

Reaction Conditions

Reaction Steps

A 1.0 M tetrahydrofuran solution of borane (81.5 mL, 81.5 mmol) was added to a flask containing anhydrous tetrahydrofuran (450 mL) under a nitrogen atmosphere. The solution was cooled to −10° C. using an ice/salt water bath. ((10-undecenyl)-ethoxyphosphinyl)methylphosphonic acid dimethyl ester (30 g, 81.4 mmol) was added slowly to the borane solution. The reaction mixture was stirred at −10° C. for 15 minutes and then warmed to ambient temperature and stirred for 2 hours. The solution was again cooled to −10° C. and 1N NaOH (81.4 mL, 81.4 mmol) was added dropwise in a manner that controlled the frothing. This addition was followed by the addition of a 30 wt % hydrogen peroxide solution (28.6 g). This mixture was then heated to 50° C. for 2 hours and then allowed to cool to ambient temperature. The excess peroxide was then reduced by the addition of aqueous sodium bisulfite (22 g in 120 mL water). The volatiles were removed by rotary evaporation to give a viscous liquid. The liquid was dissolved in ethyl acetate (800 mL) and then extracted twice with water (500 mL). The water layer was collected and extracted with ethyl acetate (600 mL). The organic extracts were combined and dried over sodium sulfate. The solvent was then removed by rotary evaporation revealing a viscous liquid. The liquid was placed under high vacuum to remove remaining volatiles providing the desired product (28.5 g, 90% yield). 1H NMR (400 MHz CDCl3): δ 4.0 (m, 2H), 3.7 (m, 6H), 3.5 (t, 2H), 2.3 (m, 2H), 1.8 (m, 2H), 1.5 (m, 4H), 1.2 (m, 18H).

Provenance & Evidence