Selective Synthesis of 4,4′-Dimethylbiphenyl
from 2‑Methylfuran
Posted on 2021-02-17 - 17:56
4,4′-Dimethylbiphenyl (DMBP)
is a promising platform chemical
for the production of polymer precursors, plasticizers, and metal–organic
frameworks among other materials. We report a two-step process to
produce DMBP from 2-methylfuran (MF) via the formation of the intermediate
5,5′-dimethyl-2,2′-bifuran (DMBF). DMBF is generated
from the Pd-catalyzed oxidative coupling of MF in the presence of
trifluoroacetic acid (TFA) with high selectivity (94%). Optimization
of reaction conditions yields a 20-fold increase in site-time-yield
(STY = 6.99 h–1) compared with a previously reported
protocol. High O2 pressure (7 bar) and a high TFA concentration
(3 M) are critical to improve the DMBF formation rate. For the conversion
of DMBF to DMBP, we show that phosphoric acid supported on silica
(P-SiO2) catalyzes tandem Diels–Alder and dehydration
reactions of DMBF with ethylene to produce DMBP (83% yield). The high
yield and selectivity are a consequence of the weak Brønsted
acid sites in P-SiO2 that dehydrate furan-ethylene cycloadducts
without substantial formation of carbon deposits.
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Cho, Hong Je; Kuo, Mi Jen; Ye, Mingchun; Kurz, Yannick; Yuan, Yong; Lobo, Raul F. (2021). Selective Synthesis of 4,4′-Dimethylbiphenyl
from 2‑Methylfuran. ACS Publications. Collection. https://doi.org/10.1021/acssuschemeng.0c09227