Acetic Anhydride → 4-ACETOXY-3-NITROHEXANE

HRID 244295Notes

Reaction equation

HRID 244295 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

4-hydroxy-3-nitrohexane (14.7 g, 100 mmol), acetic anhydride (14.8 ml, 157.3 mmol), chloroform (50 ml), and several drops of concentrated sulfuric acid were fed into a reaction vessel, and the mixture was stirred at room temperature for 10 hours. After the completion of the reaction, chloroform (50 ml) was added, and washed with water, a 5% aqueous solution of sodium bicarbonate, and a saturated salt solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 4-acetoxy-3-nitrohexane (16.3 g, 86% yield).

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c4222f2d3ad49d6bca5cdf400cc39d2
Source dataset
uspto-grants-2014_02
Patent number
US08658459B2

Reaction notes

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