Nitric Acid → HCID 86738433, compound

HRID 1074883Notes

Reaction equation

HRID 1074883 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].S(=O)(=O)(O)O.[OH:10][CH2:11][CH:12]([CH2:15][OH:16])[CH2:13][OH:14]>C(Cl)Cl>[N+:1]([O-:4])([OH:3])=[O:2].[N+:1]([O-:4])([OH:3])=[O:2].[N+:1]([O-:4])([OH:3])=[O:2].[OH:10][CH2:11][CH:12]([CH2:15][OH:16])[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 78432Trimethylolmethane

Product 1

HCID 86738433HCID 86738433, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methylene chloride (150 ml) and a 1:1 mixture of anhydrous nitric acid and 30% fuming sulfuric acid (40 ml) carefully stirred at 10° to 15%C. is added portionwise 2-hydroxymethyl-1,3-propanediol (7.5 g) while measuring the redox potential of the solution and maintaining it between -0.07 and 0.20 volts. This is conveniently done with an Ingold Redox probe charged with the mixed acid. When the addition is complete the phases are separated, the organic phase washed with water, aqueous sodium bicarbonate and aqueous urea, dried over sodium sulfate and/or molecular sieves and the solvent evaporated to give the title product (15 g) m.p. 11°-12° C.,D 1.53,nD29.5 1.4746.

Workup

  1. temperaturemaintaining it between -0.07 and 0.20 volts
  2. additioncharged with the mixed acid
  3. additionWhen the addition
  4. customare separated
  5. washthe organic phase washed with water, aqueous sodium bicarbonate and aqueous urea
  6. dry with materialdried over sodium sulfate and/or molecular sieves
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-65853e3dbf19461e98793ea9bde87cd9
Source dataset
uspto-grants-1983_07
Patent number
US04394329

Reaction notes

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