Dichloromethane → 4-(Nitrooxy)butanoic acid

HRID 2118109Notes

Reaction equation

HRID 2118109 reaction equation
C(Cl)Cl.[N+:4]([O-:7])([OH:6])=[O:5].OS(O)(=O)=O.O[CH2:14][CH2:15][CH2:16][C:17]([O-:19])=[O:18].[K+]>O>[N+:4]([O:7][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 23689651Potassium oxybateHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 98340014-(Nitrooxy)butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

CH2Cl2 (10 ml) was added to the HNO3/H2SO4 mixture, and the resulting solution was stirred for 15 minutes. Potassium 4-(hydroxy)butanoate (500 mg, 3.52 mmol) was then added in small portions to the methylenechloride solution kept at 0-5° C. The mixture was kept under stirring for 6 hours while the temperature was allowed to reach 25° C. gradually. Water (50 ml) was added to the reaction mixture and the resulting mixture was extracted with CH2Cl2 (3×25 ml). The combined organic phases were washed with water, dried over MgSO4 and concentrated to dryness under reduced pressure. 4-(Nitrooxy)butanoic acid was obtained as a yellow oil (300 mg, 57%) and used in the next step.

Workup

  1. customkept at 0-5° C
  2. stirringunder stirring for 6 hours while the temperature
  3. customto reach 25° C.
  4. extractionthe resulting mixture was extracted with CH2Cl2 (3×25 ml)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1a8adeb2957544b8af872a0616c3452a
Source dataset
uspto-grants-2008_10
Patent number
US07442826B2

Reaction notes

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