Iodine → 4-Iodo-1,2-dimethoxybenzene

HRID 34291

Reaction equation

HRID 34291 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[I:11]I>C(O)C>[I:11][C:7]1[CH:8]=[C:1]([O:9][CH3:10])[C:2]([O:3][CH3:4])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 807Iodine2×HCID 7043Veratrole

Product 1

HCID 2303074-Iodo-1,2-dimethoxybenzeneYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of veratrole (28.0 ml, 0.22M) in 95% ethanol (75 ml) was heated to 60° C. and, while stirring, was treated with iodine (50 g, 0.197M) and yellow mercuric oxide (30.0 g, 0.1385M). The iodine and mercuric oxide were added alternately in small portions over a period of 1.5 hours. After the addition was complete, the cooled mixture was filtered through Celite and concentrated. The residue was taken up in Et2O and again filtered. The Et2O solution was washed with solutions of sodium thiosulfate, 2N NaOH, saturated NaCl, dried over anhydrous K2CO3 and evaporated. The residue was distilled under reduced pressure to give 40.88 g, bp 110°-112° C. (2mm) pure 4-iodoveratrole [70% yield, literature: Gutzke et al., J. Org. Chem. 22, 1271 (1957), bp 80°-85° C. (1 mm)]. NMR (CDCl3) δ 3.80 ppm (s, 6H, (2x) OCH3), 6.57 (d, 1H, ArH6), 7.20 (m, 2H, ArH3 and ArH5).

Workup

  1. additionAfter the addition
  2. filtrationthe cooled mixture was filtered through Celite
  3. concentrationconcentrated
  4. filtrationagain filtered
  5. washThe Et2O solution was washed with solutions of sodium thiosulfate, 2N NaOH, saturated NaCl
  6. dry with materialdried over anhydrous K2CO3
  7. customevaporated
  8. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-3cbcc5b6c21949b6933dc413ab3fab04
Source dataset
uspto-grants-1988_08
Patent number
US04761413

Linked notes

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