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

HRID 2417624Notes

Reaction equation

HRID 2417624 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:18])[CH:12]([N+:15]([O-:17])=[O:16])[CH2:13][OH:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:19](OC(=O)C)(=[O:21])[CH3:20].[C:26](Cl)(=[O:28])[CH3:27]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([O:18][C:26](=[O:28])[CH3:27])[CH:12]([N+:15]([O-:17])=[O:16])[CH2:13][O:14][C:19](=[O:21])[CH3:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 134689041-(3,4-Dimethoxyphenyl)-2-nitropropane-1,3-diol

Product 1

HCID 134688891-(3,4-Dimethoxyphenyl)-2-nitro-1,3-diacetoxypropaneYield 65.1%

Conditions

Temperature
50 °C

Procedure

A mixture of 12.85 g (0.05 moles) of 1-(3,4-dimethoxyphenyl)-2-nitro-1,3-propanediol, 20.4 g of acetic anhydride and 3.92 g of acetyl chloride is stirred at 50° C. for 5 hours. The mixture is cooled and poured onto ice. The resulting oily substance is washed twice with ice-cold water and decanted. Crystallization sets in after adding 20 ml of isopropanol to the substance. The separated crystalline product is filtered off, washed thrice with 5 ml of isopropanol and 10 ml of n-hexane, each, and dried. 11.1 g (65.1%) of the title compound are obtained; m.p.: 85°-88° C.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto ice
  3. washThe resulting oily substance is washed twice with ice-cold water
  4. customdecanted
  5. customCrystallization sets
  6. additionin after adding 20 ml of isopropanol to the substance
  7. filtrationThe separated crystalline product is filtered off
  8. washwashed thrice with 5 ml of isopropanol and 10 ml of n-hexane
  9. customeach, and dried

Sources & evidence

ORD record
ord-9436253ee65643eab2465b7a7ffc9dac
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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