Water → 4-Hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone

Participants

Reaction Conditions

Reaction Steps

To the compound [VIII-1] (28.3 g, 0.12 mole) obtained above are added water (1200 g) and acetic acid (1.5 g), and the pH value thereof is adjusted to pH 4.4 with 5 % aqueous sodium hydroxide solution. The mixture is heated, with stirring at 100° C. for 25 hours. After completion of the reaction, the reaction solution is cooled and extracted twice with methyl isobutyl ketone (300 ml). The extract is separated and concentrated to give a mixture (21.5 g, yield; 76 %) of 4-hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone (racemic 4-hydroxycyclopentenone) and 3-hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone [IX-1] (ratio thereof=6:4).

Provenance & Evidence