Acetic Anhydride → 4-ACETOXY-3-NITROHEXANE

HRID 1712238Notes

Reaction equation

HRID 1712238 reaction equation
[OH:1][CH:2]([CH2:9][CH3:10])[CH:3]([N+:6]([O-:8])=[O:7])[CH2:4][CH3:5].[C:11](OC(=O)C)(=[O:13])[CH3:12]>S(=O)(=O)(O)O.C(Cl)(Cl)Cl>[C:11]([O:1][CH:2]([CH2:9][CH3:10])[CH:3]([N+:6]([O-:8])=[O:7])[CH2:4][CH3:5])(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 2206384-Nitro-3-hexanol

Product 1

HCID 117693024-ACETOXY-3-NITROHEXANEYield 86.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent2×

Procedure

A reaction vessel was charged with 4-hydroxy-3-nitrohexane (14.7 g, 100 mmol), acetic anhydride (14.8 ml, 157.3 mmol), chloroform (50 ml) and a few drops of concentrated sulfuric acid, then stirred for 10 hours at room temperature. After the reaction was finished, chloroform (50 ml) was added, and the resulting solution was washed with water, 5% aqueous sodium bicarbonate solution and saturated saline. The obtained organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, whereby 4-acetoxy-3-nitrohexane (16.3 g, yield 86%) was obtained.

Workup

  1. washthe resulting solution was washed with water, 5% aqueous sodium bicarbonate solution and saturated saline
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-336c8b807255441bb7d5191bccb3c183
Source dataset
uspto-grants-2010_09
Patent number
US07791069B2

Reaction notes

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