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

HRID 1612992Notes

Reaction equation

[OH2:1].[OH-].[Na+].[OH:4][C:5]1[CH2:9][CH2:8][C:7](=O)[C:6]=1[CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>C(O)(=O)C>[OH:1][CH:8]1[CH2:9][C:5](=[O:4])[C:6]([CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

To the compound [VIII-1] (28.3 g, 0.12 mole) 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) and separated. Methyl isobutyl ketone is distilled off from the organic layer 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).

Workup

temperatureThe mixture is heated
customAfter completion of the reaction
temperaturethe reaction solution is cooled
extractionextracted twice with methyl isobutyl ketone (300 ml)
customseparated
distillationMethyl isobutyl ketone is distilled off from the organic layer

Sources & evidence

ORD record: ord-2cb228ef929b4902a78803f319fa7a56
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05191109

Reaction notes

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