Nitric Acid → 5-nitrooxypentanoic Acid

HRID 1625585Notes

Reaction equation

HRID 1625585 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])([OH:8])=[O:7].Br[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]>ClCCl>[N+:6]([O:9][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 163685-Bromovaleric acid

Product 1

HCID 117884725-nitrooxypentanoic AcidYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Concentrated sulphuric acid 96% (1.24 mL, 2.0 eq) was added dropwise to fuming nitric acid 100% (0.97 mL, 2.0 eq) at 0° C. After 10 minutes of stirring at 0° C., a solution of 1 (2.00 g, 1.0 eq) in dichloromethane (20.0 mL) was added dropwise. The reaction mixture was stirred from 0° C. to RT for 3 hours and quenched with water (30.0 mL). The organic layer was washed with water (20.0 mL) and brine (20.0 mL), dried over magnesium sulphate, filtered off and concentrated under vacuum. The residue was adsorbed on silica gel and purified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (10CV*), 97/3 (5CV)] affording compound 2 as a colourless liquid (1.47 g, yield=58%).

Workup

  1. stirringThe reaction mixture was stirred from 0° C. to RT for 3 hours
  2. customquenched with water (30.0 mL)
  3. washThe organic layer was washed with water (20.0 mL) and brine (20.0 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered off
  6. concentrationconcentrated under vacuum
  7. custompurified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (10CV*), 97/3 (5CV)]

Sources & evidence

ORD record
ord-33007dca86cc48a094244523273f975f
Source dataset
uspto-grants-2014_07
Patent number
US08784871B2

Reaction notes

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