Benzyl chloromethyl ether → 1-Benzyloxymethylimidazole

HRID 261934Notes

Reaction equation

HRID 261934 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Na].Cl[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1>[CH2:10]([O:9][CH2:8][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 137983Benzyl chloromethyl etherHCID 57373095Imidazole sodium

Product 1

HCID 147959081-Benzyloxymethylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 58 g. of imidazole-sodium in 200 ml. of anhydrous tetrahydrofuran 100 g. of benzyl chloromethyl ether were added drop-wise with stirring at a temperature of 0° to 5° C. Cooling was discontinued after one hour. The mixture was left standing overnight and thereafter concentrated. The residue was treated with 2 N hydrochloric acid solution and with diethyl ether. The acidic aqueous layer was made alkaline with potassium carbonate and extracted with chloroform. The chloroform layer was treated with activated carbon, dried and concentrated. The residue was subjected to distillation. Boiling point 147° C./3 mm.Hg.

Workup

  1. temperatureCooling
  2. waitThe mixture was left
  3. waitstanding overnight
  4. concentrationconcentrated
  5. additionThe residue was treated with 2 N hydrochloric acid solution and with diethyl ether
  6. extractionextracted with chloroform
  7. additionThe chloroform layer was treated with activated carbon
  8. customdried
  9. concentrationconcentrated
  10. distillationThe residue was subjected to distillation

Sources & evidence

ORD record
ord-cf1141d491fa41afae0b2b8768d6dd13
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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