Sodium Hydroxide → 2,2-Dimethyl-5-nitro-1,3-dioxane

HRID 232399Notes

Reaction equation

HRID 232399 reaction equation
[CH3:1][C:2]1([CH3:13])[O:7][CH2:6][C:5](CO)([N+:8]([O-:10])=[O:9])[CH2:4][O:3]1.[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]1([CH3:13])[O:3][CH2:4][CH:5]([N+:8]([O-:10])=[O:9])[CH2:6][O:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 300859(2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol

Product 1

HCID 108774282,2-Dimethyl-5-nitro-1,3-dioxaneYield 107.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Into a 250 ml round bottom flask equipped with a stir bar, thermometer and reflux condensor topped with a nitrogen inlet was added 5.73 g (0.03 mole) of 2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane and 70 ml 10% sodium hydroxide which was heated to 60° C. for one hour. The solution was cooled to 5° C. and at this temperature acidified to pH 5 with concentrated acetic acid. The precipitated solid was filtered off and dried to give 5.2 g (92%) of 2,2-dimethyl-5-nitro-1,3-dioxane m.p. 60°-61° C. 1H NMR in CD3OD also confirmed the structure.

Workup

  1. customInto a 250 ml round bottom flask equipped with a stir bar
  2. temperaturethermometer and reflux condensor
  3. customtopped with a nitrogen inlet
  4. temperatureThe solution was cooled to 5° C. and at this temperature
  5. filtrationThe precipitated solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-3ca6b5527b844164a0799330a60b4ad2
Source dataset
uspto-grants-1989_07
Patent number
US04851588

Reaction notes

Loading…