2,5-DIMETHOXYBENZENE-1,4-DIACETONITRILE synthesis
- Product Name:2,5-DIMETHOXYBENZENE-1,4-DIACETONITRILE
- CAS Number:38439-93-9
- Molecular formula:C12H12N2O2
- Molecular Weight:216.24
Yield:38439-93-9 70 %
Reaction Conditions:
in dimethyl sulfoxide at 50 - 85;Inert atmosphere;
Steps:
2,2′-(2,5-Dimethoxy-1,4-phenylene)diacetonitrile (16):
To a mechanicallystirred suspension of NaCN (3.45 g, 70.5 mmol) in anhydrousdimethylsulfoxide was added in small portions of 15 (7.11 g, 30.2mmol). The reaction mixture was stirred at 50 C for 1 h. Temperaturewas increased to 85 C and the reaction mixture was allowed to stir atthat temperature for additional 5 min. The mixture was cooled to rt. Thereaction mixture was diluted with water (100 mL) and extracted withethyl acetate (3 X 150 mL). The combined organic layer was washedwith water, brine, dried over Na2SO4, and solvent was removed undervacuum. Crude product was purified by column chromatography using20 % ethyl acetate in hexane to give compound 16 (4.57 g, 21.2 mmol,70 %) as white solid. 1H NMR (600 MHz, CDCl3): δ 6.92 (s, 2H), 3.85 (s,6H), 3.70 (s, 4H),.
References:
Dinda, Bidyut;Das, Banibrata;Biswas, Swati;Sharma, Horrick;Armstrong, Christopher;Yedlapudi, Deepthi;Antonio, Tamara;Reith, Maarten;Dutta, Aloke K. [Bioorganic and Medicinal Chemistry,2023,vol. 78,art. no. 117131]
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