Acetyl chloride → 4,4-Dinitrobutyl acetate

HRID 1199508Notes

Reaction equation

HRID 1199508 reaction equation
[N+:1]([CH:4]([N+:9]([O-:11])=[O:10])[CH2:5][CH2:6][CH2:7][OH:8])([O-:3])=[O:2].[C:12](Cl)(=[O:14])[CH3:13]>C(Cl)Cl>[C:12]([O:8][CH2:7][CH2:6][CH2:5][CH:4]([N+:9]([O-:11])=[O:10])[N+:1]([O-:3])=[O:2])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 144017664,4-Dinitrobutan-1-ol

Product 1

HCID 144017674,4-Dinitrobutyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This ester was synthesized by treating a solution of 4,4-dinitro-1-butanol (39.2 g, 0.24 mols) in CH2Cl2 (100 ml) with acetyl chloride (22 ml, 24 g, 0.31 mol). After 90 minutes at room temperature, the reaction was quenched with ice water. Separation, drying (MgSO4), and concentration of the organic phase gave the product (42.7 g, 87%) as a light yellow oil; nD =1.4574 (24C). The infrared spectrum of the product had peaks at 2960, 1745, 1575, 1245, and 1060 cm-1. Elemental analyses-Calculated for C6H10N2O6 : C, 34.95; H, 4.85; N, 13.59; Found: C, 35.17; H, 4.83; N, 12.95.

Workup

  1. customthe reaction was quenched with ice water
  2. customSeparation
  3. dry with materialdrying (MgSO4), and concentration of the organic phase

Sources & evidence

ORD record
ord-cf1ae0a1194d4a8491da65d770a89a86
Source dataset
uspto-grants-1990_02
Patent number
US04900851

Reaction notes

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