Nitrogen → Racemic 1,3,5-Tris(1-(4-hydroxyphenyl)ethyl)benzene

Participants

Reaction Conditions

Reaction Steps

A 250 mL round-bottomed flask equipped with magnetic stirring bar was charged with racemic 1,3,5-tris(1-(4-methoxyphenyl)ethyl)benzene (5) (19.6 g, 41 mmol) and pyridine hydrochloride (56.8 g, 0.49 mol, 12 equiv). The mixture was protected with an N2 bubbler and heated in a 180° C. oil bath for 5 h. The mixture was allowed to cool briefly to ˜120° C. and then 55° C. H2O (100 mL) was added slowly to the mixture with vigorous stirring. The mixture was extracted three times with EtOAc (100 mL portions). The collected organic phase was washed with brine (200 mL) and dried over anhydrous MgSO4. Rotary evaporation gave a thick, colorless oil that foamed under vacuum. Yield: 17.17 g (95%). 1H NMR (300 MHz, DMSO-d6, δ, ppm): 9.12 (s, 3OH), 6.98 (d, J=8.6 Hz, 6H), 6.90 (s, 3H), 6.63 (d, J=8.6 Hz, 6H), 3.92 (q, J=7.2 Hz, 3H), 1.44 (d, J=7.5 Hz, 9H). 13C NMR (75 MHz, DMSO-d6, δ, ppm): 155.35, 146.59, 146.53, 146.48, 136.69, 136.67, 136.65, 128.04, 123.88, 123.65, 114.96, 43.49, 43.46, 22.09, 22.04. Anal. calcd for C30H30O3.0.65H2O: C, 80.02; H, 7.01. Found: C, 80.38; H, 7.41.

Provenance & Evidence