Iodine → p-Iodocumene

HRID 990320Notes

Reaction equation

HRID 990320 reaction equation
[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.[I:12](O)(=O)=O>C(O)(=O)C.O.ClCCl.S(=O)(=O)(O)O>[CH:7]([C:1]1[CH:6]=[CH:5][C:4]([I:12])=[CH:3][CH:2]=1)([CH3:9])[CH3:8]

Participants

8

Reactant 3

HCID 807IodineHCID 7406CumeneHCID 24345Iodic acid

Product 1

HCID 87073p-IodocumeneYield 94%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
85 °C

Procedure

(C9H11I), FW=246.09 g/mol. Cumene (45.0 g, 377 mmol), iodine (38.25 g, 151 mmol) and iodic acid (15.38 g, 87.4 mmol) were dissolved in a solution of acetic acid (188 mL), water (30 mL), dichloromethane (19 mL), and sulfuric acid (7.5 mL). The solution was heated to 85° C. for three hours. Once the reaction was complete, the reaction was worked up with water and dichloromethane. The dichloromethane was washed with sodium hydrosulfite, dried over magnesium sulfate and concentrated, yielding a red liquid in 94% yield. Rf 0.63 (hexanes) 1H NMR (300 MHz, CDCl3, ppm) d 7.58 (d, 2H, J=8.3 Hz), 6.96 (s, 2H, J=8.3 Hz), 2.83 (septet, 1H, J=6.9 Hz), 1.20 (d, 6H, J=6.9 Hz); 13C NMR (75.5 MHz, CDCl3, ppm) d 148.2, 137.2, 128.5, 90.7, 33.6, 23.8; LR MS (EI) m/z 246.

Workup

  1. washThe dichloromethane was washed with sodium hydrosulfite
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customyielding a red liquid in 94% yield

Sources & evidence

ORD record
ord-be77e1872bb24443a8659c078f2530a3
Source dataset
uspto-grants-2002_10
Patent number
US06458967B1

Reaction notes

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