Iodine → 2-Iodo-9,10-dihydrophenanthrene

HRID 511057Notes

Reaction equation

HRID 511057 reaction equation
[CH:1]1[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[I:15](O)(=O)(=O)=O.II.S(=O)(=O)(O)O>C(O)(=O)C.O>[I:15][C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 130589,10-DihydrophenanthreneHCID 65185Metaperiodic acid

Product 1

HCID 576345402-Iodo-9,10-dihydrophenanthrene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

25.0 g (0.139 mol) of 9,10-dihydrophenanthrene, 6.30 g (27.6 mmol) of periodic acid and 17.0 g (67.0 mmol) of iodine are heated at 70° C. for 1 h in a solution of 4 ml of conc. sulfuric acid and 28 ml of water in 140 ml of glacial acetic acid. The solution is subsequently added to ice-water and extracted three times with ethyl acetate. The combined org. phases are washed with sat. sodium hydrogencarbonate soln. and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is distilled in a bulb tube at 170° C. and 0.3 mbar, giving 2-iodo-9,10-dihydrophenanthrene as yellow oil.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washphases are washed with sat. sodium hydrogencarbonate soln
  3. dry with materialand dried over sodium sulfate
  4. customThe solvent is removed in vacuo
  5. distillationthe residue is distilled in a bulb tube at 170° C.

Sources & evidence

ORD record
ord-573aff8fea804694b7513a4b92e9d3fb
Source dataset
uspto-grants-2015_08
Patent number
US09096795B2

Reaction notes

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