Potassium Carbonate → HCID 11485672, compound

Participants

Reaction Steps

The O-alkylation procedure described for 190 was used. To a stirred suspension of 4,4′-[(3,3,5,5-tetramethylcyclohexylidene)methanediyl]diphenol (219) (0.600 g, 1.78 mmol), K2CO3 (0.368 g, 2.67 mmol), and acetone (60 mL) was added bromoacetonitrile (0.200 mL, 2.85 mmol) under a nitrogen atmosphere at RT. The reaction mixture was refluxed for 3 h, cooled to RT and filtered. Standard work-up followed by purification afforded 0.196 g (29%) of the title compound 229 as a white solid along with 0.38 g (52%) of the bis-alkylated compound 2,2′-[[(3,3,5,5-tetramethylcyclohexylidene)methanediyl]bis(benzene-4,1-diyloxy)]diacetonitrile. In addition, 0.10 g of unreacted starting material (19) was recovered. 1H NMR (300 MHz, CDCl3): δ 7.15 (d, J=8.7 Hz, 2H), 7.04 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 6.76 (d, J=8.4 Hz, 2H), 4.75 (s, 2H), 2.00 (s, 2H), 1.98 (s, 2H), 1.31 (s, 2H), 0.95 (s, 12H). LCMS (ESI): m/z 374 (M−H)−. Anal. Calcd for C25H29NO2, C, 79.96; H, 7.78; N, 3.73. Found: C, 79.95; H, 7.84; N, 3.73.

Provenance & Evidence