Acetyl chloride → 1-(4-Nitrophenyl)-2-nitro-1,3-diacetoxypropane

HRID 2417626Notes

Reaction equation

HRID 2417626 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:17])[CH:11]([N+:14]([O-:16])=[O:15])[CH2:12][OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:18](OC(=O)C)(=[O:20])[CH3:19].[C:25](Cl)(=[O:27])[CH3:26]>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:17][C:25](=[O:27])[CH3:26])[CH:11]([N+:14]([O-:16])=[O:15])[CH2:12][O:13][C:18](=[O:20])[CH3:19])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 134689051-(4-Nitrophenyl)-2-nitro-1,3-propanediol

Product 1

HCID 134688901-(4-Nitrophenyl)-2-nitro-1,3-diacetoxypropaneYield 211.7%

Conditions

Temperature
60 °C

Procedure

A mixture of 8.5 g (0.035 moles) of 1-(4-nitrophenyl)-2-nitro-1,3-propanediol, 14 g (0.13 moles) of acetic anhydride and 1 g of acetyl chloride is stirred at 60° C. for 3 hours. The mixture is cooled, poured onto 60 g of ice and stirred thoroughly. Water is decanted, 10 ml of isopropanol are added to the waxy residue, and the substance is crystallized at 0° C. The separated crystalline product is filtered off, washed with isopropanol and dried at 20° C. 8.8 g (77%) of the title compound are obtained; m.p.: 63°-66° C.

Workup

  1. temperatureThe mixture is cooled
  2. stirringstirred thoroughly
  3. customWater is decanted
  4. addition10 ml of isopropanol are added to the waxy residue
  5. customthe substance is crystallized at 0° C
  6. filtrationThe separated crystalline product is filtered off
  7. washwashed with isopropanol
  8. customdried at 20° C

Sources & evidence

ORD record
ord-b3a928914eb54be5b4aa5486fc0f4d07
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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