Pyridine → 3-Phenoxybenzyl chloride

HRID 1659802Notes

Reaction equation

HRID 1659802 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:24])=O>C(Cl)(Cl)Cl>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 262953-Phenoxybenzyl alcohol

Product 1

HCID 932913-Phenoxybenzyl chlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 200 g. of m-phenoxy-benzyl alcohol in 1 liter of dry chloroform 2 ml. of pyridine are added and a solution of 142.8 g. thionyl-chloride in 150 ml. of chloroform is added dropwise under cooling with ice water. When the addition is completed the cooling is terminated and the solution is allowed to warm up to room temperature under stirring and the temperature is maintained under stirring until the vigorous gas evolution ceases. The mixture is then boiling under stirring until the gas evolution ceases completely. The solution is then poured into 2 liters of cold water, the chloroform layer is separated and the aqueous layer is shaken out in 400 ml. of chloroform. The combined chloroform solutions are washed once with water and dried above sodium sulphate. The drying agent is filtered off and chloroform is distilled off; thus 210 g. (96%) of m-phenoxy-benzyl chloride are obtained, which can be distilled at 128° to 130° C. at a pressure of 0.3 mmHg. Substantially no forerun and residue are obtained.

Workup

  1. additionWhen the addition
  2. customis terminated
  3. temperaturethe temperature is maintained
  4. stirringunder stirring until the vigorous gas evolution ceases
  5. stirringunder stirring until the gas evolution
  6. additionThe solution is then poured into 2 liters of cold water
  7. customthe chloroform layer is separated
  8. stirringthe aqueous layer is shaken out in 400 ml
  9. washThe combined chloroform solutions are washed once with water
  10. dry with materialdried above sodium sulphate
  11. filtrationThe drying agent is filtered off
  12. distillationchloroform is distilled off

Sources & evidence

ORD record
ord-bc3ba8886cba4d6b91006029d2686552
Source dataset
uspto-grants-1981_12
Patent number
US04304930

Reaction notes

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