Iodine → HCID 20470550, compound

HRID 1388243Notes

Reaction equation

HRID 1388243 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[I:17](O)(=O)=O.II.S(=O)(=O)(O)O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.O.C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

9

Reactant 5

HCID 807Iodine2×HCID 1118Sulfuric AcidHCID 24345Iodic acidHCID 24477Sodium ThiosulfateHCID 204705634-(2-Methoxyethyl)-1,1'-biphenyl

Product 1

HCID 20470550HCID 20470550, compoundYield 231%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
83 °C

Procedure

Into a 300 ml three-neck flask were added 4-(β-methyloxyethyl) biphenyl (34 g, 0.16 mol), acetic acid (112 ml), water (30 ml), iodic acid (6.8 g, 0.0384 mol), iodine (17.9 g, 0.0704 mol), carbon tetrachloride (13 ml) and conc. sulfuric acid (4.8 ml). The mixture was warmed by a mantle heater with stirring, and reaction was carried out under reflux at 83° C. for 3 hours. After completion of the reaction, the reaction liquid was cooled down to 70° C., and 10% sodium thiosulfate aqueous solution (10 ml) was added to cause excess iodine to disappear. The liquid was cooled down to room temperature, and the precipitated crystals were recrystallized from ethyl ethanol (300 ml) to obtain 4'-(β-methoxyethyl)-4-iodobiphenyl (V) (30 g) having a melting point of 97°~99.4° C.

Workup

  1. temperatureThe mixture was warmed by a mantle heater
  2. customreaction
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. temperaturewas cooled down to 70° C.
  6. temperatureThe liquid was cooled down to room temperature
  7. customthe precipitated crystals were recrystallized from ethyl ethanol (300 ml)

Sources & evidence

ORD record
ord-dca8434e973242e29f4406eec8532ad8
Source dataset
uspto-grants-1984_02
Patent number
US04431564

Reaction notes

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