2,2-Dimethoxypropane → (2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol

HRID 1111258

Reaction equation

HRID 1111258 reaction equation
[OH:1][CH2:2][C:3]([CH2:9][OH:10])([CH2:7][OH:8])[N+:4]([O-:6])=[O:5].CO[C:13](OC)([CH3:15])[CH3:14]>Cl.C(#N)C>[CH3:14][C:13]1([CH3:15])[O:8][CH2:7][C:3]([CH2:9][OH:10])([N+:4]([O-:6])=[O:5])[CH2:2][O:1]1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 31337Tris(hydroxymethyl)nitromethane

Product 1

HCID 300859(2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanolYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a 250 ml round bottom flask equipped with a stir bar was added 5 g (0.03 mol) tris(hydroxymethyl) nitromethane, 3.75 g (0.36 mol) 2,2-dimethoxypropane, 100 ml acetonitrile and 6 drops concentrated hydrochloric acid. The reaction was heated to 80° C. for 18 hours. After cooling to room temperature tte volatiles were removed in vacuo to give a white solid 2,2-dimethyl-5-hydroxy methyl-5-nitro-1,3-dioxane in 82% yield.

Workup

  1. customTo a 250 ml round bottom flask equipped with a stir bar
  2. temperatureAfter cooling to room temperature tte volatiles
  3. customwere removed in vacuo

Sources & evidence

ORD record
ord-4cb4e03e4c7a4972819b706c2c63d137
Source dataset
uspto-grants-1990_12
Patent number
US04978793

Linked notes

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