2 3 dichloro 5 6 dicyano p benzoquinone ddq

Analytical reagents were all employed without further purification. Mash Premiere for Pharmaceutical Industries (Badr city, Egypt) provided pharmaceutical grade atomoxetine hydrochloride and p-chloranil (Sigma Chemical Co., USA) 200 mg of p-chloranil were dissolved in a 100 mL volumetric flask with acetonitrile as the solvent to create 0.2% w/v. 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (Sigma Chemical Co., USA) 0.3% w/v is produced by combining 300 mg of DDQ with acetonitrile and dissolving it in a 100 mL standard flask. El Nasr Chemical Co. provided the ethanol, methanol, acetonitrile, 1,4-dioxane, and dimethylformamide that were purchased (Abu Zaabal, Egypt).

Vanillate, guaiacol, GSH, and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) were purchased from Sigma-Aldrich. erythro-GGE was purchased from TCI America (Portland, OR).
A racemic mixture of MPHPV was synthesized by dissolving erythro-GGE into ethyl acetate (Fisher) and then slowly adding 1.25 molar eq of DDQ and stirring for 30 min. The reaction was washed three times with saturated NaHCO₃ to remove DDQH₂ formed during the reaction. The MPHPV was purified via flash chromatography using hexane/ethyl acetate (0.33:0.67, v/v), as described previously (15 (link)), and then crystallized from the eluent via solvent evaporation.
HPV was synthesized as described previously for synthesis of β-deoxy-α-veratrylglycerone, except using 4-O-benzyl-acetovanillone as starting material, rather than acetoveratrone (15 (link)). Synthesis of HPV required an additional debenzylation step that was unnecessary in the synthesis of β-deoxy-α-veratrylglycerone.