Triethylamine → 3-Nitrooxy-propyl propionate

HRID 1776948Notes

Reaction equation

HRID 1776948 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N+:6]([O:9][CH2:10][CH2:11][CH2:12][OH:13])([O-:8])=[O:7].C(N(CC)CC)C>>[C:1]([O:13][CH2:12][CH2:11][CH2:10][O:9][N+:6]([O-:8])=[O:7])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 100118933-Nitrooxypropanol

Product 1

HCID 716187393-Nitrooxy-propyl propionate

Conditions

Temperature
3 °C

Procedure

9.1 mmol Propionyl chloride were dissolved in 10 ml TMBE and cooled to 3° C. 8.25 mmol 3-Nitrooxypropanol and 9.1 mmol triethylamine in 5 ml TMBE were dropped over a period of 5 min at 3 to 6° C. After 2 hours and 30 minutes stirring without cooling the reaction mixture were extracted with 1N HCl, twice with water, washed with brine, dried over Na2SO4 and the solvent was removed in vacuo leaving 1.35 g.

Workup

  1. temperaturewithout cooling the reaction mixture
  2. extractionwere extracted with 1N HCl, twice with water
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customleaving 1.35 g

Sources & evidence

ORD record
ord-13f5218e071a4db9895e100498acb3de
Source dataset
uspto-grants-2016_02
Patent number
US09266814B2

Reaction notes

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