Methanol → 1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid

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Reaction Steps

Hydrolysis of this ester to the title compound is effected as follows: The ester is dissolved in 230 ml. of methanol. To this is added 10 g. of KOH in 30 ml. of H2O and the solution is allowed to stand at room temperature overnight. The methanol is evaporated, water added and the solution washed with benzene. The aqueous phase is acidified with 6N HCl, and extracted with benzene. This organic phase is washed with water, dried over sodium sulfate and evaporated to dryness to give an oil, which is crystallized from benzene containing a trace of petroleum ether to afford the title compound, m.p. 150 - 152° C., νmaxCHCl3 3325 and 1705 cm-1.

Provenance & Evidence