Diethyl 2-(4-methoxyphenyl)malonate → 2-(4-Methoxyphenyl)-1,3-propanediol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

LiAlH4 (5.75 g, 0.15 mol) was suspended in ethyl ether (150 mL), and into this suspension solution compound 19 (16.85 g, 0.10 mol) dissolved in 50 ml ethyl ether was added dropwise. The resulting solution was stirred at 40° C. for 40 hr, and cooled in ice bath, and ethyl ether (15 ml) was introduced dropwise to destroy the excess LiAlH4 remaining in the solution. After the addition was completed, the resulting solution was added with 200 ml HCl aqueous solution (HCl/H2O, 1:2) and stirred for one hr. The organic phase was removed. The aqueous phase was extracted with ethyl ether (2×200 ml). The ether layer was combined with the collected organic phase, and then was washed with NaHCO3 aqueous solution (2%, 20 ml), water (20 ml), saturated sodium chloride solution (20 ml), dried, and filtered. The residual was recrystallized from benzene to yield 12 g (66%) product 20. 1 H-NMR (CDCl3, TMS, δ in ppm): 2.17 (s, 2H, --OH), 3.08 (m, 1H PhCH), 6.82 and 7.13 (q, 4 aromatic protons).

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