2,3-Dimethoxy-1,4-naphthoquinone → HCID 20403098, compound

HRID 2164719Notes

Reaction equation

HRID 2164719 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].CO[C:7]1[C:8](=[O:20])[C:9]2[C:14]([C:15](=[O:19])[C:16]=1[O:17][CH3:18])=[CH:13][CH:12]=[CH:11][CH:10]=2.[NH4+].[Cl-].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>[Cl-].[Cl-].[Zn+2]>[CH3:18][O:17][C:16]1[C:15](=[O:19])[C:14]2[C:9]([C:8](=[O:20])[C:7]=1[CH2:25][CH2:24][CH2:23][CH2:27][CH2:9][CH2:8][CH2:7][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

6

Reactant 4

HCID 31362,3-Dimethoxy-1,4-naphthoquinoneHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20403098HCID 20403098, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To 0.216 g (1.62 mmoles) of AlCl3 in 50 mL of THF was added 7.0 g (0.697 mmoles/g in THF, 4.88 mmoles) of dodecyl MgBr. This mixture was added dropwise to 1.27 g (9.34 mmoles) of ZnCl2 and 1.00 g (4.67 mmoles) of 2,3-dimethoxy-1,4-naphthoquinone in 50 mL of THF. The mixture was stirred overnight, poured into 100 mL of NH4Cl solution, extracted with 3×50 mL of ether, dried over MgSO4, filtered, and solvent was removed by rotary evaporation. The residue was chromatographed on silica gel eluted with toluene. Thus, 0.034 g (0.096 mmoles, 2.1%) of 2-methoxy-3-dodecylnaphthoquinone was obtained.

Workup

  1. extractionextracted with 3×50 mL of ether
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customsolvent was removed by rotary evaporation
  5. customThe residue was chromatographed on silica gel
  6. washeluted with toluene

Sources & evidence

ORD record
ord-581aba924ef24389b604445cff161a5b
Source dataset
uspto-grants-1985_03
Patent number
US04507241

Reaction notes

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