Pyridine → 2,6-Bis(chloromethyloxy-carbonyloxymethyl)pyridine

HRID 34983

Reaction equation

HRID 34983 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[N:10]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:6][CH2:5][O:4][C:2]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:2]([O:4][CH2:5][Cl:6])=[O:3])[N:10]=1)=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 709572,6-Pyridinedimethanol2×

Product 1

HCID 147495552,6-Bis(chloromethyloxy-carbonyloxymethyl)pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The reaction of the compound of the formula (II) with the compound of the formula (III) is carried out at a temperature between -30° C. and +10° C., preferably at about -5° C. This reaction will be described in detail hereinafter. At least 2 moles of chloromethyl chloroformate of the formula (III) [as calculated for 2,6-bis(hydroxymethyl)pyridine of the formula (II)] are dissolved in the desired solvent, preferably in chloroform, and a solution containing an organic base, preferably pyridine, in the same molar amount as the compound of the formula (III) in the same solvent is added at a temperature lower than 10° C., preferably at about -5° C., under stirring. The suspension obtained is stirred for about 20 minutes while care is taken to avoid any increase of the temperature. Then, 2,6-bis(hydroxymethyl)pyridine of the formula (II) is added to the above mixture at the same temperature at such a rate that the temperature reaches at most -5° C. The suspension is stirred for about 20 minutes to give a brown solution. After washing this solution with water and evaporation, a practically pure product with 95 to 97% of 2,6-bis(chloromethyloxy-carbonyloxymethyl)pyridine content is obtained. The product obtained after washing with water and making free of the solvent can be used without any purification or, if desired, may be further purified by chromatography on a silicagel column or on an other adsorbent, e.g. on a synthetic resin.

Workup

  1. customis carried out at a temperature between -30° C. and +10° C., preferably at about -5° C
  2. customThis reaction
  3. customThe suspension obtained
  4. stirringis stirred for about 20 minutes while care
  5. temperatureany increase of the temperature
  6. customreaches at most -5° C
  7. stirringThe suspension is stirred for about 20 minutes
  8. customto give a brown solution
  9. washAfter washing this solution
  10. customwith water and evaporation

Sources & evidence

ORD record
ord-d0a7d882a5dc4a7cae8c601d5f4403b6
Source dataset
uspto-grants-1988_08
Patent number
US04764613

Linked notes

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