Hydrochloric Acid → 3-(10H-Anthracen-9-ylidenemethyl)-phenol

Participants

Reaction Conditions

Reaction Steps

Mix 9-(3-methoxy-benzylidene)-9,10-dihydro-anthracene (900 mg, 3.0 mmol) and pyridine hydrochloride (4 g) and heat at 220° C. for 30 minutes. Cool to 115° C. and carefully add 5N HCl. Extract the product into EtOAc, dry (MgSO4) the organic solution and concentrate to give 720 mg dark oil. Purify by ISCO using EtOAc/hexanes to give title compound, mp 195.8° C., HPLC>99% purify. MS (es) 283 (M−1). 1H NMR (DMSO -d6) □3.74 (br s, 1H), 6.79-7.45 (m, 13H), 9.46 (s, 1H); 13C NMR (DMSO-d6) δ 40.22, 114.59, 115.81, 119.51, 125.53, 125.85, 127.02, 127.30, 128.05, 128.27, 128.56, 129.77, 129.06, 129.39, 134.75, 135.83, 138.98, 139.92, 142.87, 144.63, 157.27

Provenance & Evidence