7-(2,6-Dichloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuran → HCID 13246037, compound

Participants

Reaction Steps

To a solution of 29.2 g of 3,5-dichloro-4-(2,3-dihydro-2,2-dimethyl-7-benzofuranyloxy)-1-nitrobenzene in 500 ml of toluene was added 2.3 g of 5% platinum on carbon catalyst. This mixture was then charged into a 1 L rocking Parr reactor. The reactor was purged twice with nitrogen then twice with hydrogen, then finally filled with hydrogen to a pressure of 100 psig. The hydrogen pressure was maintained between 75 and 100 psig during the course of the reaction. After hydrogen uptake ceased, the reaction mixture was removed from the reactor. This was filtered through celite. Removal of the solvents afforded 23.95 g of off-white crystals. mp 140°-145° C. NMR (CDCl3): 1.53 (s, 6H), 3.03 (s, 2H), 3.70 (broad s, 2H), 6.2-7.0 (M, 5H, contains singlet at 6.62).

Provenance & Evidence