Sodium Iodide → 1,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-(4-nonynyl)benzene

HRID 1588170Notes

Reaction equation

HRID 1588170 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].C([Li])(CC)C.Br[CH2:25][CH2:26][CH2:27][C:28]#[C:29][CH2:30][CH2:31][CH2:32][CH3:33].[I-].[Na+]>O1CCCC1.C(OCC)(=O)C.CCCCCC.C1C=CC=CC=1.C(OCC)C.CN(C)P(=O)(N(C)C)N(C)C>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([O:15][CH2:16][O:17][CH3:18])[C:3]([O:2][CH3:1])=[C:8]([CH2:25][CH2:26][CH2:27][C:28]#[C:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:7]=1[O:9][CH2:10][O:11][CH3:12]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 10061046HCID 10061046, compoundHCID 109765551-Bromo-4-nonyneHCID 178418400CID 53628100

Product 1

HCID 197571921,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-(4-nonynyl)benzene

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolventHCID 21226206Ethyl acetate hexaneSolventHCID 22174802Benzene etherSolvent

Conditions

Temperature
-78 °C

Procedure

3.0 Grams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in 500 ml of anhydrous tetrahydrofuran, this solution was cooled to -78° C. on a dry ice-acetone bath under an atmosphere of argon gas. To this solution was added dropwise 10.7 ml of secbutyllithium (1.3M cyclohexane solution), and stirred for 30 minutes. Then 3.54 g of 1-bromo-4-nonyne was added dropwise thereto, further 2.1 g of sodium iodide and 60 ml of hexamethylphosphoric triamide were added to the reaction mixture and stirred for 12 hours at room temperature. Tetrahydrofuran was removed under reduced pressure, then to the residue obtained was added 300 ml of mixed solvent of benzene-diethyl ether (1:1). The organic layer was washed four times with 100 ml of water, and washed four times with 100 ml of a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate then the solvent was removed under reduced pressure. The residue obtained was treated by means of a silica gel column chromatography (diameter: 5.5 cm×length 15.5 cm, "Wakogel C-200", developing and eluting solvent: 20% ethyl acetate-n-hexane). There was obtained 1.4 g of 1,4-dimethoxy-2,5-bis(methoxymethoxy)-3-(4-nonynyl)benzene as in the form of colorless oily substance.

Workup

  1. stirringstirred for 12 hours at room temperature
  2. customTetrahydrofuran was removed under reduced pressure
  3. customto the residue obtained
  4. washThe organic layer was washed four times with 100 ml of water
  5. washwashed four times with 100 ml of a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue obtained

Sources & evidence

ORD record
ord-7b87cfbfbbf446aa9a473991a5466dbd
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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