Thionyl Chloride → 4-Chloro-4-oxobutyl nitrate

HRID 2118110Notes

Reaction equation

HRID 2118110 reaction equation
S(Cl)([Cl:3])=O.[N+:5]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)([O-:7])=[O:6]>CCOCC.CN(C=O)C>[N+:5]([O:8][CH2:9][CH2:10][CH2:11][C:12]([Cl:3])=[O:14])([O-:7])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 98340014-(Nitrooxy)butanoic acid

Product 1

HCID 136544364-Chloro-4-oxobutyl nitrate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (0.6 ml, 7.7 mmol) was slowly added, under stirring and under argon, to a solution of 4-(Nitrooxy)butanoic acid (1.00 g, 6.7 mmol) in anhydrous Et2O (25 ml) kept 0° C. A few drops of DMF (4-5 drops) were also added under stirring to the reaction mixture and the reaction temperature was allowed to rise to r.t. (ca. 20° C.). The reaction mixture was stirred at room temperature and under argon for 5 hours. The reaction mixture was concentrated in vacuo to provide crude 4-(nitrooxy)butanoyl chloride.

Workup

  1. customkept 0° C
  2. customto rise to r.t.
  3. custom(ca. 20° C.)
  4. stirringThe reaction mixture was stirred at room temperature and under argon for 5 hours
  5. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d5dd152eb9054569b68c196a0538d226
Source dataset
uspto-grants-2008_10
Patent number
US07442826B2

Reaction notes

Loading…