Sodium Iodide → 4,4-Diphenylbutyl iodide

HRID 1598801

Reaction equation

HRID 1598801 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[I-:19]>CC(=O)CC>[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10][I:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 122234581,1-Diphenyl-4-bromobutane

Product 1

HCID 155128794,4-Diphenylbutyl iodide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1,1-diphenyl-4-bromobutane (2.5 g, 12 mmol) and NaI (11.9 g, 80 mmol) in 2-butanone (70 ml) was heated for 4 hours at reflux. The solvent was removed in vacuo and the residue was taken up in Et2O (100 ml). The organic layer was washed with aqueous Na2SO3 (10%) and with brine, dried (Na2SO4), and concentrated in vacuo. The oil was distilled under high vacuum to obtain the title compound, bp 150° C./0.1 mm.

Workup

  1. temperaturewas heated for 4 hours
  2. temperatureat reflux
  3. customThe solvent was removed in vacuo
  4. washThe organic layer was washed with aqueous Na2SO3 (10%) and with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. distillationThe oil was distilled under high vacuum

Sources & evidence

ORD record
ord-2673d3b97a6d474ea6520eb7763f233e
Source dataset
uspto-grants-1998_04
Patent number
US05739164

Linked notes

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