Benzyl Chloride → 1-(Benzyloxy)-4-iodobenzene

HRID 1660684Notes

Reaction equation

HRID 1660684 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 5196711-(Benzyloxy)-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A reaction mixture composed of 21.40 g (95.3 mmol) of 98% 4-iodophenol, 12.19 g (95.3 mmol) of 99% benzyl chloride, 20.73 g (150 mmol) of potassium carbonate and 250 ml of acetone was heated to reflux temperature and heated to boiling for 30 hours. After cooling to room temperature, the reaction mixture was filtered. The filtrate was concentrated and then cooled in an ice bath, in the course of which a solid precipitated out. This was removed by means of a blue-band filter and then dried. The crude product (23.22 g) was recrystallized from 70 ml of ethanol. 17.20 g (58% of theory) of colorless microcrystals having an m.p. of 61-62° C. (lit. 62° C.) were obtained.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature
  3. temperatureheated
  4. filtrationthe reaction mixture was filtered
  5. concentrationThe filtrate was concentrated
  6. temperaturecooled in an ice bath, in the course of which a solid
  7. customprecipitated out
  8. customThis was removed by means of a blue-band filter
  9. customdried
  10. customThe crude product (23.22 g) was recrystallized from 70 ml of ethanol
  11. customan m.p. of 61-62° C. (lit. 62° C.)
  12. customwere obtained

Sources & evidence

ORD record
ord-eee27b9e4fe147dd8e55086696d664d8
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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