Formaldehyde → 1-Nitro-2-phenylethane

HRID 424292

Reaction equation

HRID 424292 reaction equation
C(O)(=O)C.C(O)(=O)C.C(NCCNCC1C=CC=CC=1)C1C=CC=CC=1.[N+:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]CCCCCCCCCC)([O-:29])=[O:28].C=O>C1(C)C=CC=CC=1.CO>[N+:27]([CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 312281,2-Ethanediamine, N1,N2-bis(phenylmethyl)-, acetate (1:2)HCID 115439441-Nitrooctadecane

Product 1

HCID 802081-Nitro-2-phenylethaneYield 222.9%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

In a 500 mL round-bottom flask N,N′-dibenzylethylenediamine diacetate (4.78 g, 13 mmol) and 1-nitrooctadecane (3, 3.97 g, 13 mmol) are dissolved in 1:1 toluene/methanol (100 mL). Paraformaldehyde (1.39 g, 46.5 mmol) is added portion wise to the solution and the resulting suspension is refluxed. The mixture becomes homogeneous (dissolution of paraformaldehyde) and after 3 h at reflux, the mixture is cooled and evaporated in vacuo. The residue is recrystallized from ethanol, obtaining pure 4 (4.38 g, 61%) as colorless solid. M.p. 70-72° C. (EtOH), ESI-MS: 586 (MNa+), 564 (MH+); (Calc. for C36H57N3O2: 563 u.m.a.).

Workup

  1. temperaturethe resulting suspension is refluxed
  2. temperatureafter 3 h at reflux
  3. temperaturethe mixture is cooled
  4. customevaporated in vacuo
  5. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-1d182a84b662451e802d4458c69ed212
Source dataset
uspto-grants-2012_01
Patent number
US08105567B2

Linked notes

Loading…