Hydrochloric Acid → HCID 178495623, compound

HRID 1262482Notes

Reaction equation

HRID 1262482 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[I:16](O)(=O)=O.II.Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCCCCCC.C(Cl)(Cl)(Cl)Cl.O.C(O)(=O)C>[CH3:1][O:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 807Iodine2×HCID 24345Iodic acidHCID 24477Sodium ThiosulfateHCID 178495619HCID 178495619, compound

Product 1

HCID 178495623HCID 178495623, compoundYield 210.4%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8900HeptaneSolvent

Procedure

Into a 1 l three-neck flask were added compound (D) (100.0 g, 0.489 mol), acetic acid (344 ml), water (91 ml), iodic acid (20.6 g, 0.117 mol), iodine (54.5 g, 0.215 mol), CCl4 (40 ml) and conc. hydrochloric acid (14 ml), followed by stirring and further refluxing for 3 hours while heating on a mantle heater. After cooling, a 10% aqueous solution of sodium thiosulfate (15 ml) was added to cause the color of excess iodine to disappear, followed by adding n-heptane (200 ml ), transferring the mixture into a separating funnel, washing the resulting n-heptane layer with water till the aqueous layer becomes neutral, distilling off n-heptane under reduced pressure, dissolving the residue in n-hexane (50 ml), allowing the solution to stand at -10° to -20° C. for 12 hours, filtering off the resulting crystals and drying to obtain 4-(trans-4'-methyloxymethylcyclohexyl)iodobenzene (E) (81.3 g). M.P. 40.3°~ 42.3° C.

Workup

  1. temperaturefurther refluxing for 3 hours
  2. temperaturewhile heating on a mantle heater
  3. temperatureAfter cooling
  4. washwashing the resulting n-heptane layer with water till the aqueous layer
  5. distillationdistilling off n-heptane under reduced pressure
  6. dissolutiondissolving the residue in n-hexane (50 ml)
  7. filtrationfiltering off the resulting crystals
  8. customdrying

Sources & evidence

ORD record
ord-f117b39ac07a4a1c94f1eb121be7b599
Source dataset
uspto-grants-1984_06
Patent number
US04452719

Reaction notes

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