Iodine → Benzene, 1-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy-

HRID 1856595Notes

Reaction equation

HRID 1856595 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][O:11][CH2:12][C:13]#[CH:14])=[CH:5][CH:4]=1.[OH-].[Na+].[I:17]I>CO>[I:17][C:14]#[C:13][CH2:12][O:11][CH2:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 15480687HCID 15480687, compound

Product 1

HCID 10267888Benzene, 1-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy-Yield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methoxy-4-[(2-propynyloxy)methoxy]benzene (Intermediate II-a) (9.8 g, 0.5 mol) prepared in the above example 2 and 48% w/v aqueous sodium hydroxide solution (11.0 g) were added to methanol (75 g). Iodine (14.0 g, 0.055 mol) was then added to the solution in several portions during which the inner temperature was maintained at below 10° C. The reaction mixture was stirred for further 3 hours and the solvent was then evaporated off. The residue was extracted with toluene (20 ml) and the toluene layer was washed with distilled water. Toluene was then evaporated off to obtain the desired 1-[[(3-iodo-2-propynyl) oxy]methoxy]-4-methoxybenzene (Derivative III-a)(12.6 g).

Workup

  1. temperaturewas maintained at below 10° C
  2. customthe solvent was then evaporated off
  3. extractionThe residue was extracted with toluene (20 ml)
  4. washthe toluene layer was washed with distilled water
  5. customToluene was then evaporated off

Sources & evidence

ORD record
ord-7b9981aeff2640e2bc389e57dc3a1cbc
Source dataset
uspto-grants-2000_11
Patent number
US06143311

Reaction notes

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