Acetic Anhydride → 4-ACETOXY-3-NITROHEXANE

HRID 909992Notes

Reaction equation

HRID 909992 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 the whole was washed with water, a 5% aqueous solution of baking soda, and a saturated salt solution. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to yield 4-acetoxy-3-nitrohexane (16.3 g, 86% yield).

Workup

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

Sources & evidence

ORD record
ord-66f1ef01fbf2413c8ba4f6dada0dc89b
Source dataset
uspto-grants-2011_09
Patent number
US08021915B2

Reaction notes

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