Benzoyl chloride → 3-Nitrooxy-propyl benzoate

HRID 1776949Notes

Reaction equation

HRID 1776949 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][OH:8])([O-:3])=[O:2].C(N(CC)CC)C.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:16]([O:8][CH2:7][CH2:6][CH2:5][O:4][N+:1]([O-:3])=[O:2])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 100118933-Nitrooxypropanol

Product 1

HCID 679811703-Nitrooxy-propyl benzoate

Conditions

Temperature
3 °C

Procedure

16.5 mmol 3-Nitrooxypropanol dissolved in 10 ml TMBE and 18.2 mmol Triethylamine were cooled to 3° C. 18.2 mmol benzoylchloride in 5 ml TMBE were dropped over a period of 7 minutes at 3 to 6° C. After 24 hours and 30 minutes stirring without cooling, the reaction mixture was extracted with sated. NaHCO3, water, 1N HCl, twice with water, washed with brine, dried over Na2SO4 and the solvent was removed in vacuo leaving 3.3 g.

Workup

  1. temperaturewithout cooling
  2. extractionthe reaction mixture was extracted with sated
  3. washNaHCO3, water, 1N HCl, twice with water, washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customleaving 3.3 g

Sources & evidence

ORD record
ord-23e3b67cda234d4bacffa43236eaf013
Source dataset
uspto-grants-2016_02
Patent number
US09266814B2

Reaction notes

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