Oxalyl chloride → 5-Chloro-5-oxopentyl nitrate

HRID 422894Notes

Reaction equation

HRID 422894 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)([O-:3])=[O:2].C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C=O)C>[N+:1]([O-:3])([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([Cl:15])=[O:11])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 117884725-nitrooxypentanoic Acid

Product 1

HCID 212769385-Chloro-5-oxopentyl nitrateYield 82.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(Nitrooxy)pentanoic acid (489 mg, 3.00 mmol; US Patent 2006/189603) was dissolved in anhydrous DCM (30 mL) under N2, cooled to 0° C., and added in succession anhydrous DMF (1 drop) and oxalyl chloride (262 uL, 3.00 mmol). Allowed to stir at ambient temperature for 12 h. 13CNMR displayed acid chloride (δ171 ppm) with small amount of carboxylic acid (˜δ173 ppm). Evaporated and dried in vacuo to yield 450 mg (80%) of 5-chloro-5-oxopentyl nitrate as light yellow oil, which was used without further purification.

Workup

  1. customEvaporated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-ab2a72140e3440fdbb7a7dbe860ef65c
Source dataset
uspto-grants-2012_01
Patent number
US08101658B2

Reaction notes

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