Triethylamine → 3-Nitrooxy-propyl 5-nitrooxy-hexanoate

HRID 1776951Notes

Reaction equation

HRID 1776951 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][OH:8])([O-:3])=[O:2].[CH2:9](N(CC)CC)C.[N+:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25])([O-:18])=[O:17]>C(OCC)C>[N+:16]([O:19][CH:20]([CH3:9])[CH2:21][CH2:22][CH2:23][C:24]([O:8][CH2:7][CH2:6][CH2:5][O:4][N+:1]([O-:3])=[O:2])=[O:25])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100118933-NitrooxypropanolHCID 212769385-Chloro-5-oxopentyl nitrate

Product 1

HCID 885402503-Nitrooxy-propyl 5-nitrooxy-hexanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

20 mmol 3-Nitrooxypropanol dissolved in 10 ml Diethylether and 20 mmol Triethylamine were cooled to 0° C. 18.2 mmol 5-nitrooxypentoylchlorid were dropped over a period of 5 min at 0 to 5° C. After stirring over night without cooling, the reaction mixture was extracted with 1N HCl, twice with water, washed with brine, dried over Na2SO4 and the solvent was removed in vacuo.

Workup

  1. temperaturewithout cooling
  2. extractionthe reaction mixture was extracted with 1N HCl, twice with water
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e5e42d10eb7045f9a12bc42b292b08fb
Source dataset
uspto-grants-2016_02
Patent number
US09266814B2

Reaction notes

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