Pyridine → 2-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin

HRID 1388682Notes

Reaction equation

HRID 1388682 reaction equation
S(Cl)([Cl:3])=O.N1C=CC=CC=1.O[CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[O:15][CH2:14]1>O>[Cl:3][CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[O:15][CH2:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 193141,4-Benzodioxane-2-methanolHCID 24386Thionyl Chloride

Product 1

HCID 953202-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a three neck flask fitted with a stirring device, 218 g thionyl chloride are mixed with 1000 g pyridine while cooling. They are added further, portionwise 500 g 2(hydroxy methyl) (2,3-dihydro [4H] 1,4-benzodioxin) while keeping the inner temperature below 20°. When the reaction is completed, the mixture is heated at 100° for 3 hours then poured into water and extracted with chloroform. The solvent is distilled off and the raw residue is purified by fractional distillation under reduced pressure. 340 g of the chloromethylated derivative are obtained. It boils at 85°-90°/0.2 mm Hg.

Workup

  1. temperaturewhile cooling
  2. additionThey are added further
  3. customthe inner temperature below 20°
  4. temperaturethe mixture is heated at 100° for 3 hours
  5. extractionextracted with chloroform
  6. distillationThe solvent is distilled off
  7. distillationthe raw residue is purified by fractional distillation under reduced pressure
  8. custom340 g of the chloromethylated derivative are obtained

Sources & evidence

ORD record
ord-15bea4e132154133b50f22aeb21c79f6
Source dataset
uspto-grants-1984_02
Patent number
US04432984

Reaction notes

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