Sodium Iodide → 1-(4-Iodobutyl)-2,3,4,5-tetramethoxy-6-methylbenzene

HRID 1074576Notes

Reaction equation

HRID 1074576 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]O)=[C:7]([CH3:14])[C:6]([O:15][CH3:16])=[C:5]([O:17][CH3:18])[C:4]=1[O:19][CH3:20].C(N(CC)CC)C.CS(Cl)(=O)=O.[I-:33].[Na+]>C(Cl)Cl.CC(C)=O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][I:33])=[C:7]([CH3:14])[C:6]([O:15][CH3:16])=[C:5]([O:17][CH3:18])[C:4]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20495945HCID 20495945, compound

Product 1

HCID 131875351-(4-Iodobutyl)-2,3,4,5-tetramethoxy-6-methylbenzeneYield 94%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In anhydrous methylene chloride (300 ml) were 1,2,3,4-tetramethoxy-5-methyl-6-(4-hydroxybutyl)benzene (28.2 g, 0.1 mole) as obtained in Reference Example 59 and triethylamine (16 g, 0.15 mole), and the solution was cooled to 0° C. A solution of methanesulfonyl chloride (14.3 g, 0.12 mole) in methylene chloride (30 ml) was added dropwise to the solution, followed by stirring for 30 minutes. The reaction solution was washed with water, dilute aqueous phosphoric acid and water, successively, and the organic layer was dried (over MgSO4) and freed of the solvent. Acetone (300 ml) and sodium iodide (39.0 g, 0.26 mole) were added to the residue, and the mixture was warmed at 50° C. for 2 hours. After the completion of the reaction, acetone was distilled off under reduced pressure, and isopropyl ether (300 ml) and water (200 ml) were added to the residue for extraction of the product. The organic layer was washed with 5% aqueous sodium hydrosulfite and water, successively, and dried (over MgSO4), followed by distilling off the solvent under reduced pressure. The residue was chromatographed on a column of silica gel, and developing with isopropyl ether-hexane (1:1) yielded 1,2,3,4-tetramethoxy-5-methyl-6-(4-iodobutyl)benzene (37.0 g, 94%).

Workup

  1. washThe reaction solution was washed with water, dilute aqueous phosphoric acid and water
  2. dry with materialsuccessively, and the organic layer was dried (over MgSO4)
  3. temperaturethe mixture was warmed at 50° C. for 2 hours
  4. distillationwas distilled off under reduced pressure, and isopropyl ether (300 ml) and water (200 ml)
  5. additionwere added to the residue for extraction of the product
  6. washThe organic layer was washed with 5% aqueous sodium hydrosulfite and water
  7. dry with materialsuccessively, and dried (over MgSO4)
  8. distillationby distilling off the solvent under reduced pressure
  9. customThe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-09709cc9c2514020aa07095ee09b6647
Source dataset
uspto-grants-1983_07
Patent number
US04393075

Reaction notes

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