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

HRID 1612988Notes

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) 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).

Workup

customTo the compound [VIII-1] (28.3 g, 0.12 mole) obtained
temperatureThe mixture is heated
customAfter completion of the reaction
temperaturethe reaction solution is cooled
extractionextracted twice with methyl isobutyl ketone (300 ml)
customThe extract is separated
concentrationconcentrated

Sources & evidence

ORD record: ord-09d7e22e56944914b669c1c46993b765
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05191109

Reaction notes

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