Toluene → HCID 20798726, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dihydroxynaphthalene (500 g, 3.125 mol) and maleic anhydride (765 g, 7.815 mol, 2.5 eq) in 1 L 1:1 1,2-dichlorobenzene:toluene were heated at 110° C. for 3 days. The reaction mixture was then cooled to 90° C., 1.5 L ethyl acetate added, and then further cooled to room temperature overnight. The mixture was then cooled over ice after another 0.5 L ethyl acetate was added and left stirring for 2 hours. The resultant solid was isolated by filtration, washed with 2×200 mL cold ethyl acetate and dried in oven at 40° C. to provide 130 g of the anhydride as a beige solid (16% yield). 1H NMR (acetone-d6) 7.33 (d, J=8.2 Hz, 1H), 6.97 (d, J=2.3 Hz, 1H), 6.85 (dd, J=8.1, 2.4 Hz, 4.05 (d, J=3.9 Hz, 1H), 3.98 (dd, J=6.0, 2.9 Hz, 1H), 3.88 (dd, J=10.2, 3.9 Hz, 1H), 3.70 (dd, J=10.2, 2.7 Hz, 1H), 2.39 (br s, 2H). HRMS for MH+259.0600 (theoretical 259.0606).

Provenance & Evidence