2-Methyl-2-nitro-1,3-propanediol → 5-Methyl-5-nitro-1,3-dioxan-2-one

HRID 374865

Reaction equation

HRID 374865 reaction equation
[CH3:1][C:2]([N+:7]([O-:9])=[O:8])([CH2:5][OH:6])[CH2:3][OH:4].[C:10]1(=O)OCC[O:11]1>C(OCC)(=O)C>[CH3:1][C:2]1([N+:7]([O-:9])=[O:8])[CH2:5][O:6][C:10](=[O:11])[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 64802-Methyl-2-nitro-1,3-propanediolHCID 7303Ethylene carbonate

Product 1

HCID 189960545-Methyl-5-nitro-1,3-dioxan-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-2-nitro-1,3-propanediol and ethylene carbonate is heated overnight. The reaction mixture is diluted with ethyl acetate and the solution is washed with water. The organic phase is dried and concentrated to obtain 5-methyl-5-nitro-1,3-dioxan-2-one. This is dissolved in methanol and hydrogenated under pressure to give the 5amino compound which is acylated with dodecanoyl chloride to give the product.

Workup

  1. washthe solution is washed with water
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-95f89e8157fe4d36923e6412f8b53d05
Source dataset
uspto-grants-1996_01
Patent number
US05482965

Linked notes

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