Potassium Bromide → alpha-(3,5-Di-tert-butyl-4-hydroxyphenyl)-N-(3-phenylpropyl)-aminomethylphosphonic acid

HRID 21617Notes

Reaction equation

HRID 21617 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([NH:25][CH2:26][P:27](=[O:34])([O:31]CC)[O:28]CC)[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[K+].[Br-]>O>[C:12]([C:9]1[CH:8]=[C:7]([CH:16]([NH:25][CH2:26][P:27](=[O:28])([OH:34])[OH:31])[CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 86748728Diethyl alpha-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-(3-phenylpropyl)aminomethylphosphonate2×

Product 1

HCID 86748727alpha-(3,5-Di-tert-butyl-4-hydroxyphenyl)-N-(3-phenylpropyl)-aminomethylphosphonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

Workup

  1. temperatureat reflux in 30 ml NHCl for 24 h
  2. extractionThe compound was extracted with chloroform
  3. custom2.5 g were obtained
  4. customYield =94%, mp=162°-169° C

Sources & evidence

ORD record
ord-9a5b0306fe3c416398af18b29d37cc24
Source dataset
uspto-grants-1995_06
Patent number
US05424303

Reaction notes

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