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

Participants

Reaction Conditions

Reaction Steps

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%.

Provenance & Evidence