Reaction #49895

Reaction equation

Diethyl α-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-(3-phenylpropyl)aminomethylphosphonate

compound 22

Diethyl α-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-(3-phenylpropyl)aminomethylphosphonate

KBr

→

α-(3,5-Di-tert-butyl-4-hydroxyphenyl)-N-(3-phenylpropyl)-aminomethylphosphonic acid

Solvents

H2O

Conditions

Workup

1. 1
   Temperatureat reflux in 30 ml NHCl for 24 h
2. 2
   ExtractionThe compound was extracted with chloroform
3. 3
   Other2.5 g were obtained
4. 4
   OtherYield =94%, mp=162°-169° C

Procedure

Diethyl α-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-(3-phenylpropyl)aminomethylphosphonate (compound 22, 3.0 g, 6.1 mmol) was heated at reflux in 30 ml NHCl for 24 h. The compound was extracted with chloroform, 2.5 g were obtained. Yield =94%, mp=162°-169° C. IR (KBr) 3640 cm-1 : OH, 3400 (broad): NH, 2800 and 1600: PO-H, 1430: tert-Bu, 1200: P=O, 1000 and 940: P--OH Elemental analysis: C24H36NO4P. % Calc. C 66.49 H 8.37 N 3.23 P 7.14 % Found C 66.69 H 8.52 N 2.95 P 6.91 0.2 % H2O

Source