Chloride → 4-Chloro-4-oxobutyl nitrate

HRID 1374690Notes

Reaction equation

HRID 1374690 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:12].[Cl-]>C(Cl)Cl>[N+:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]([Cl:12])=[O:10])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 312ChlorideHCID 24819Phosphorus pentachlorideHCID 98340014-(Nitrooxy)butanoic acid

Product 1

HCID 136544364-Chloro-4-oxobutyl nitrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a three neck flask kept under argon and containing 90 ml of CH2Cl2, 4-nitrooxybutanoic acid (800 mg, 5.3 mmol) prepared as described above was charged. Then PCl5 was added in one portion (1.25 g, 6.0 mmol) and the resulting mixture was stirred at room temperature. The reaction was checked by IR spectroscopy. After ca. 2 hours stirrer was removed and the reaction mixture was distilled under vacuum. The crude chloride (900 mg, 5.4 mmol) was used in the further steps without purification.

Workup

  1. customprepared
  2. additionabove was charged
  3. customAfter ca. 2 hours stirrer was removed
  4. distillationthe reaction mixture was distilled under vacuum

Sources & evidence

ORD record
ord-c3d5e240402e46138ba5b1bc6479f953
Source dataset
uspto-grants-2007_01
Patent number
US07166605B2

Reaction notes

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