Potassium Carbonate → 7-(2,6-Dichloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuran

Participants

Reaction Steps

To a solution containing 32.83 g of 1,2,3-trichloro-5-nitrobenzene and 26.11 g of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran in 300 ml of methyl ethyl ketone under an atmosphere of nitrogen and at room temperature was added 21.98 g of anhydrous potassium carbonate. The reaction mixture was heated to reflux. Reflux was maintained for 30 hrs. The reaction mixture was cooled to room temperature and the solvents removed. The tan solid residue was dissolved in hot hexane containing a little ethyl acetate. This was filtered and the filtrate allowed to cool to room temperature then placed in freezer to cool further to promote crystallization. The crystals were collected and placed in a vacuum dessicator for drying. A second crop of crystals was obtained from the mother liquors. This afforded 29.2 g of pale tan crystals. mp 105°-110° C. NMR (CDCl3): 1.47 (s, 6H), 3.03 (s, 2H), 6.3-7.0 (m, 3H), 8.22 (s, 2H).

Provenance & Evidence