Iodine → HCID 21406153, compound

HRID 1016802Notes

Reaction equation

HRID 1016802 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].[I:10]I>ClC1C=CC=CC=1.[Cu](Cl)Cl>[CH2:1]([C:3]1[CH:8]=[C:7]([I:10])[CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2]

Participants

5

Reactant 2

HCID 807IodineHCID 69972-Ethylphenol

Product 1

HCID 21406153HCID 21406153, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

A solution of 119.9 ml of 2-ethylphenol in 500 ml of chlorobenzene was treated with 126.9 g of iodine and 134.5 g of copper(II) chloride and stirred under reflux for 5.5 hours. After cooling the reaction mixture was filtered and the residue was washed with methylene chloride. The combined filtrates were washed with aqueous sodium thiosulphate solution and ice-water. The organic phases were dried over sodium sulphate and concentrated. The residue was crystallized from hexane and gave 79.3 g of 2-ethyl-4-iodo-phenol. The mother liquor was chromatographed over silica gel and gave a further 41 g of 2-ethyl-4-iodo-phenol; MS (EI) m/z 248 (M).

Workup

  1. temperatureunder reflux for 5.5 hours
  2. temperatureAfter cooling the reaction mixture
  3. filtrationwas filtered
  4. washthe residue was washed with methylene chloride
  5. washThe combined filtrates were washed with aqueous sodium thiosulphate solution and ice-water
  6. dry with materialThe organic phases were dried over sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-73c1d6e5a8ae4415ba564ea407375f4c
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

Loading…