1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester → Hedione

To a reactor (a volume of 50 ml) was respectively charged 1 g (4.5 mmol) of methyl (2-pentyl-3-keto-1-cyclopentenyl-)acetate (a compound in which R1 represents an n-pentyl group and R2 represents a methyl group in the above formula (1)) and 0.2 g of each catalyst shown in Table 1. Thereto was respectively added 10 ml of a solvent shown in Table 1, and the mixture was held at a temperature shown in Table 1. Pressure reduction and hydrogen introduction were repeated while stirring the mixture, and the air in the reactor was replaced with hydrogen at ordinary pressure. The mixture was continuously stirred in this state for 4 hours. Subsequently, the catalyst was removed from the reaction mixture by filtration, and then thereto were added 30 ml of water and 30 ml of toluene followed by stirring to extract a product into the toluene phase. Toluene was distilled off from this toluene phase, yielding methyl dihydrojasmonate (a compound in which R3 represents an n-pentyl group and R4 represents a methyl group in the above formula (2)). The yield and isomer ratio (cis-isomer/trans-isomer) of the resulting methyl dihydrojasmonate were determined by gas chromatography. The results are shown in Table 1.

1. customTo a reactor (a volume of 50 ml) was respectively charged
2. stirringThe mixture was continuously stirred in this state for 4 hours
3. customSubsequently, the catalyst was removed from the reaction mixture by filtration
4. additionwere added 30 ml of water and 30 ml of toluene
5. stirringby stirring
6. extractionto extract a product into the toluene phase
7. distillationToluene was distilled off from this toluene phase

ORD record

ord-91533abe8264413092d0e1681c20032d

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897802B2