2-chloro-3-methoxynaphthalene-1,4-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). extracted with 3×50 mL of ether dried over MgSO4 filtered solvent was removed The residue was flash-chromatographed (90% toluene/hexane as eluant)