Potassium Hydroxide → 2-(7-Oxabicyclo[2.2.1]heptan-1-yl)propanoic acid

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Reaction Steps

The title compound was prepared by standard Wittig-Horner reaction from 4-hydroxy-cyclohexanone, 2-(diethoxy-phosphoryl)-propionic acid ethyl ester and sodium hydride (J. Boutagy, R. Thomas, Chem. Rev. 1974, 74, 87-99) and subsequent saponification with potassium hydroxide in ethanol. After recrystallization from n-heptane, the title compound was obtained as white solid. EI-MS: m/e=170(M+), 1H-NMR (90 MHz, CDCl3, TMS):δ 1.3 (d, J=8 Hz, 3H, Me), 1.7 (m, 8H, CH2), 3.0 (q, J=8 Hz, 1H, CH-Me), 4.6 (t, J=4.5 Hz, 1H, CH—O), 7.2 (s, 1H, COOH), mp 61-62° C., bp 120° C. (0.008 mbar).

Provenance & Evidence