Tetrahydrofuran → HCID 20403098, compound

HRID 2164717Notes

Reaction equation

HRID 2164717 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[C:8](=[O:19])[C:9]2[C:14]([C:15](=[O:18])[C:16]=1[Cl:17])=[CH:13][CH:12]=[CH:11][CH:10]=2.[NH4+].[Cl-].[CH2:22]1[CH2:26]O[CH2:24][CH2:23]1>[Cl-].[Cl-].[Zn+2]>[CH2:24]([C:7]1[C:8](=[O:19])[C:9]2[C:14]([C:15](=[O:18])[C:16]=1[Cl:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:23][CH2:22][CH2:26][CH2:9][CH2:8][CH2:7][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12].[CH2:24]([C:16]1[C:15](=[O:18])[C:14]2[C:9]([C:8](=[O:19])[C:7]=1[O:6][CH3:5])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:23][CH2:22][CH2:26][CH2:9][CH2:8][CH2:7][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 274591,4-Naphthoquinone, 2-chloro-3-methoxy-HCID 6451240Aluminum(III) Chloride

Product 2

HCID 1030502-Chloro-3-dodecyl-1,4-naphthoquinoneYield 4.6%HCID 20403098HCID 20403098, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To 0.20 g (1.50 mmoles) of AlCl3 in 20 mL of THF was added 6.80 g (4.74 mmoles, 0.697 mmoles/g) of dodecyl MgBr. This mixture was added dropwise to 0.789 g (4.49 mmoles) of 2-methoxy-3-chloro-1,4-naphthoquinone and 0.529 g (3.89 mmoles) of ZnCl2 in 50 mL of THF. The mixture was stirred overnight. The green solution was poured into 100 mL of NH4Cl solution, extracted with 3×50 mL of ether, dried over MgSO4, filtered, and solvent was removed. The residue was flash-chromatographed (90% toluene/hexane as eluant) to give 0.075 g (0.021 mmoles, 4.6%) of 2-dodecyl-3-chloronaphthoquinone and 0.246 g (0.55 mmoles, 12.3%) of 2-dodecyl-3-methoxynaphthoquinone. 1H NMR (δ, CDCl3): 8.05 (m,2H), 7.65 (m,2H), 4.10 (s,3H), 2.55 (m,2H), 1.3 (br. s,20H), 0.85 (m,3H).

Workup

  1. extractionextracted with 3×50 mL of ether
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customsolvent was removed
  5. customThe residue was flash-chromatographed (90% toluene/hexane as eluant)

Sources & evidence

ORD record
ord-0685d50eeab4447ca8edd889c3931111
Source dataset
uspto-grants-1985_03
Patent number
US04507241

Reaction notes

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