Acetyl chloride → 1-(3,4,5-Trimethoxyphenyl)-2-nitro-1,3-diacetoxy-propane

HRID 2417622Notes

Reaction equation

HRID 2417622 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([OH:20])[CH:14]([N+:17]([O-:19])=[O:18])[CH2:15][OH:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:21](OC(=O)C)(=[O:23])[CH3:22].[C:28](Cl)(=[O:30])[CH3:29]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([O:20][C:28](=[O:30])[CH3:29])[CH:14]([N+:17]([O-:19])=[O:18])[CH2:15][O:16][C:21](=[O:23])[CH3:22])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 134688871-(3,4,5-Trimethoxyphenyl)-2-nitro-1,3-propanediol

Product 1

HCID 134688881-(3,4,5-Trimethoxyphenyl)-2-nitro-1,3-diacetoxy-propaneYield 91.9%

Conditions

Temperature
60 °C

Procedure

A mixture of 9.7 g (0.0337 moles) of 1-(3,4,5-trimethoxyphenyl)-2-nitro-1,3-propanediol, 13.78 g (0.135 moles) of acetic anhydride and 2.6 g of acetyl chloride is stirred at 60° C. for 4 hours. Thereafter the mixture is cooled to 20° C. and poured onto 50 g of ice. Crystallization sets in immediately. The separated product is filtered off, washed thrice with 15 ml of ice-cold water, each, and then with a small amount (about 3 ml) of isporopanol, and dried. 11.3 g (90.12%) of the title compound are obtained; m.p.: 107°-109° C.

Workup

  1. temperatureThereafter the mixture is cooled to 20° C.
  2. customCrystallization
  3. filtrationThe separated product is filtered off
  4. washwashed thrice with 15 ml of ice-cold water
  5. customeach, and then with a small amount (about 3 ml) of isporopanol, and dried

Sources & evidence

ORD record
ord-a321ed016f36423f9436deef73d6fa14
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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