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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2308071Generated: October 30, 2026

Toluene → 2-Cyclopenten-1-one, 2-pentyl-

https://huagongshe.com/reaction/2308071

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantN-IodosuccinimideHCID 120273—
ReactantCyclopentanone, 2-(1-hydroxypentyl)-HCID 162060—
SolventWaterHCID 962—
Product2-Cyclopenten-1-one, 2-pentyl-HCID 11754985.6%

Reaction Steps

In a 50 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxypentyl)cyclopentanone (20 g) synthesized in Reference Example 1, N-iodosuccinimide (0.1 g) and toluene (10 ml), and water was removed under refluxing, followed by 4 hours of the reaction at 150° C. The reaction mixture was washed with water and the layers were separated from each other. Further, the resulting organic layer was washed with saturated brine and separated. The organic layer was evaporated on a rotary evaporator under reduced pressure to recover toluene, whereby a crude product was obtained. The product was distilled using a Claisen distillation apparatus to obtain 15.3 g of 2-pentyl-2-cyclopentenone (boiling point: 104° C./930 Pa; GC purity: 98.4%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06833481B2
Source datasetuspto-grants-2004_12
ORD IDord-4a1c660e7c0f4436ab040b4377e8448f
Source noteuspto-grants-2004_12