3-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol → a Methyl jasmonate

HRID 1732438

Reaction equation

[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([OH:11])[CH:7]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])=[O:4]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH:7]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])=[O:4]

Participants

Conditions

Temperature: 18 °C

Procedure

A 150 mg quantity of 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol is dissolved in 10 ml of methylene chloride. A 2 ml quantity of chromic acid solution of 2 M concentration is added dropwise to the solution. The mixture is stirred at about 18° C. for 12 hours and thereafter extracted with ethyl acetate. The extract is washed with aqueous solution of sodium chloride, dried and concentrated. The residue is purified with a silica gel column and distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanone (compound (4), R2 =CH3) in a yield of 88%, b.p. 92°-96° C./2.7 mm Hg.

Workup

concentrationA 2 ml quantity of chromic acid solution of 2 M concentration
additionis added dropwise to the solution
extractionextracted with ethyl acetate
washThe extract is washed with aqueous solution of sodium chloride
customdried
concentrationconcentrated
customThe residue is purified with a silica gel column
distillationdistilled in a vacuum

Sources & evidence

ORD record: ord-067fa63bb80d4e94acebb1b91ba3278b
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237308

Linked notes

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