2-(1-hydroxy-3-butenyl)-5-methyl furan → 4-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

HRID 2413374Notes

Reaction equation

[CH3:1][C:2]1[O:11][C:5]([CH:6](O)[CH2:7][CH:8]=[CH2:9])=[CH:4][CH:3]=1.P([O-])([O-])(O)=[O:13].[K+].[K+].P(=O)(O)(O)O>O>[CH2:7]([CH:6]1[C:2]([OH:11])([CH3:1])[CH:3]=[CH:4][C:5]1=[O:13])[CH:8]=[CH2:9]

Participants

Conditions

Temperature: 100 °C

Procedure

In a four-necked flask equipped with a stirrer and a thermometer, there were charged 5-methyl-α-allylfurfuryl alcohol (I-1) (152 g), water (4560 g) and a buffer solution (5.1 g) comprising potassium monohydrogen phosphate/phosphoric acid adjusted to pH 4.8, and the mixture was stirred at 100° C. for 15 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was cooled and extracted twice with methyl isobutyl ketone (600 ml). Removal of methyl isobutyl ketone from the extract gave a mixture (132.2 g) of 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (II-1) and 2-allyl-4-hydroxy-3-methyl-2-cyclopentenone (III-1). Yield, 87%.

Workup

customIn a four-necked flask equipped with a stirrer
customAfter completion of the reaction
temperaturethe reaction mixture was cooled
extractionextracted twice with methyl isobutyl ketone (600 ml)
customRemoval of methyl isobutyl ketone from the extract

Sources & evidence

ORD record: ord-9dd23631aaf7492285f5caaf66861f4f
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04496767

Reaction notes

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