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

HRID 1111255Notes

Reaction equation

HRID 1111255 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 92%

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 condenser topped with a nitrogen inlet was added 5.73 (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 condenser
  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-db567f22b07c43468c490318f9d65adb
Source dataset
uspto-grants-1990_12
Patent number
US04978793

Reaction notes

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