Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 478352Generated: October 26, 2026

Ethanol → Ethyl 4-phenyl-2-chlorobenzoate

https://huagongshe.com/reaction/478352

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantDimethylformamideHCID 6228—
ReactantTriethylamineHCID 8471—
Reactant1,3-Bis(diphenylphosphino)propaneHCID 81219—
Reactant3-Chlorobiphenyl-4-yl trifluoromethanesulfonateHCID 18001079—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
SolventHexaneHCID 8058—
ProductEthyl 4-phenyl-2-chlorobenzoateHCID 18001012—

Reaction Conditions

Temperature85 °C

Reaction Steps

To a solution of 4-phenyl-2-chloro-1-trifluoromethylsulfonyloxybenzene (35 g) in dimethylformamide (300 ml) are added palladium acetate (1.17 g), 1,3-bis(diphenylphosphino)propane (4.29 g), ethanol (91.5 ml) and triethylamine (29.0 ml) under carbon monooxide atmosphere, and the mixture is heated with stirring at 80-90° C. for 6 hours. To the reaction solution is added water, and further added a small amount of n-hexane. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed with water, dried, and the residue is purified by silica gel column chromatography (solvent; n-hexane→ethyl acetate:n-hexane=1:100) to give ethyl 4-phenyl-2-chlorobenzoate (20.9 g) as colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06642223B2
Source datasetuspto-grants-2003_11
ORD IDord-ec51087fe86f42ebbe691e01e523504a
Source noteuspto-grants-2003_11