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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1294830Generated: October 30, 2026

4-Nitrophenol → 4-(cyclopentyloxy)aniline

https://huagongshe.com/reaction/1294830

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-NitrophenolHCID 980—
ReactantDimethylformamideHCID 6228—
ReactantBromocyclopentaneHCID 8728—
ReactantPotassium CarbonateHCID 11430—
SolventWaterHCID 962—
Product4-(cyclopentyloxy)anilineHCID 6484448—

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 4-nitrophenol (63.7 g), bromocyclopentane (68.2 g), potassium carbonate (63.3 g) and DMF (300 mL) was heated at 80° C. for 24 hours. After cooling, it was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was hydrogenated in ethanol using palladium(II) hydroxide as catalyst. The product with the molecular weight of 177.25 (C11H15NO) was obtained in this way; MS (ESI): 178 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07241787B2
Source datasetuspto-grants-2007_07
ORD IDord-024e35d98a80490fa18226b209eecce1
Source noteuspto-grants-2007_07