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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 413469Generated: October 25, 2026

Water → 2-(4-(Methylthio)phenyl)acetonitrile

https://huagongshe.com/reaction/413469

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium CyanideHCID 8929—
Reactant1-(Chloromethyl)-4-(methylthio)benzeneHCID 70128—
CatalystTetrabutylammonium ChlorideHCID 70681—
SolventTolueneHCID 1140—
Product2-(4-(Methylthio)phenyl)acetonitrileHCID 2760087100.5%

Reaction Conditions

Temperature82.5 °C

Reaction Steps

Under an atmosphere of nitrogen, 25.9 g (150 mmol) of 4-(methylthio)benzyl chloride were dissolved in 45.5 g of toluene. 9.29 g (180 mmol) of sodium cyanide, 0.92 g (2.9 mmol) of tetrabutylammonium chloride and 14.4 g of water were then added. The mixture was stirred at 80-85° C. for 2 h. The reaction mixture was admixed with 30 g of toluene and 45 g of water, the aqueous phase was decanted off and the organic phase was concentrated. This gave a residue of 24.6 g of the title product in a yield of >95% (according to NMR) in the form of a pink solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06566527B1
Source datasetuspto-grants-2003_05
ORD IDord-44234c8b14c946808dc1891483781d6a
Source noteuspto-grants-2003_05