Toluene → [2-(3-Methoxyphenyl)-3,4-Dihydro-6-methoxynaphthalen-1-yl][4-hydroxyphenyl]methanone

Participants

Reaction Conditions

Reaction Steps

To EtSH (12.5 g, 14.9 mL. 0.20 mol) in anhydrous ethyl ether (300 mL) at -78° C. under a dry nitrogen atmosphere in a 1 L single neck RB flask was added slowly via syringe 1.6M n-BuLi (113 mL, 0.180 mol) over 1 hour. After addition was complete, the ether was removed under vacuum and a solution of [3,4-dihydro-6-methoxy-2-(3-methoxyphenyl)-1-naphthalenyl](4-methoxyphenyl)methanone, (24.0 g, 0.065 mol) in anhydrous DMF (150 mL) was added. The reaction mixture was heated at 70-80° C. for 2.5 hours and then at 65° C. for 20 hr. TLC analysis (SiO2, Toluene:EtOAc, 9:1) showed the starting material to be nearly gone. Two spots were present at lower Rf. These were attributed to the desired product and the corresponding diphenol (lowest spot). The reaction mixture was allowed to cool and was then poured into 500 mL iced 1N HCl solution. The crude product was extracted into EtOAc. The EtOAc phase was washed with saturated aqueous NaCl solution, dried over anhydrous MgSO4, and evaporated to a yellow oil. The product was purified by chromatography over silica gel using a gradient consisting of chloroform changing linearly to (95:5) chloroform:methanol. Following evaporation of the appropriate fractions, a yellow oil was obtained which was recrystallized from ethyl ether to yield 21.3 g, (54%) of the desired product, mp 197-8° C. 1H NMR (CDCl3) δ 7.76 (d, J=8.6 Hz, 2H), 7.10-7.00 (m, 1H), 6.90-6.70 (m, 4H), 6.70-6.60 (m, 4H), 6.07 (bs, 1H), 3.78 (s, 3H), 3.62 (s, 3H), 3.10-2.90 (m, 2H), 2.90-2.70 (m, 21H); MS (FD) m/e 386 (M+); Anal. Calc'd. for C25H22O4 : C, 77.70; H, 5.74. Found: C, 77.45; H, 5.66.

Provenance & Evidence