Dichloromethane → Chloromethyl dinitropropyl ether

HRID 1262742Notes

Reaction equation

HRID 1262742 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]([N+:12]([O-:14])=[O:13])([CH3:11])CO)([O-:7])=[O:6].[O:15]1[CH2:20]CCOO1.[Al].Cl[CH2:23][Cl:24]>>[N+:5]([CH:8]([N+:12]([O-:14])=[O:13])[CH2:11][CH2:20][O:15][CH2:23][Cl:24])([O-:7])=[O:6]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 701942,2-DinitropropanolHCID 5359268AluminumHCID 6451240Aluminum(III) ChlorideHCID 19593658CID 19593658

Product 1

HCID 57257296Chloromethyl dinitropropyl etherYield 92%

Procedure

8.8 grams of aluminum chloride was added rapidly to an ice-cooled solution of 9.9 g 2,2-dinitropropanol and 2.0 g trioxane in 50 ml dry dichloromethane under a nitrogen atmosphere. The mixture was stirred 2 days at room temperature, then it was poured onto crushed ice and the mixture stirred vigorously until all aluminum precipitates had dissolved (addition of some sulfuric acid may be required). The product solution was separated, the aqueous phase extracted with dichloromethane, and the extracts washed rapidly with a near saturated, ice cold sodium hydrogen carbonate solution. After drying (MgSO4) the solvent was evaporated in vacuo to give 12.0 g (92%) crude chloromethyl dinitropropyl ether, purity 98% by gas-liquid phase chromatography (GLPC). 1H NMR (CDCl3): δ2.18, s (3H); 4.49 (2, 2H); 5.44 (s,2H).

Workup

  1. additionit was poured
  2. customonto crushed ice
  3. customprecipitates
  4. dissolutionhad dissolved (
  5. additionaddition of some sulfuric acid
  6. customThe product solution was separated
  7. extractionthe aqueous phase extracted with dichloromethane
  8. washthe extracts washed rapidly with a near saturated, ice cold sodium hydrogen carbonate solution
  9. dry with materialAfter drying (MgSO4) the solvent
  10. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-23d5b09ec1284ad38c46266a52e35561
Source dataset
uspto-grants-1984_06
Patent number
US04453021

Reaction notes

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