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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 504333Generated: October 29, 2026

Ethylene Glycol → 1-(4-[(Trifluoromethyl)thio]phenyl}cyclopropanecarboxylic acid

https://huagongshe.com/reaction/504333

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthylene GlycolHCID 174—
Reactant1-Bromo-2-ChloroethaneHCID 7849—
Reactant4-(Trifluoromethylthio)phenylacetonitrileHCID 2777905—
ReactantSodium hydroxide--water (1/1/1)HCID 23719242—
CatalystBenzyl triethylammonium chlorideHCID 66133—
Product1-(4-[(Trifluoromethyl)thio]phenyl}cyclopropanecarboxylic acidHCID 66662204—

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of {4-[(trifluoromethyl)thio]phenyl}acetonitrile (1.15 g, 0.00529 mol), 1-bromo-2-chloro-ethane, (880 μL, 0.010 mol), benzyltriethyl ammonium chloride (70 mg, 0.0003 mol) and 1.5 ml of 50% NaOH-water (w/w) solution was kept at 50° C. with stirring for 3 hours. LCMS data supported that the reaction was complete. To the above solution 1,2-ethanediol (10 mL, 0.2 mol) was added. The mixture was heated at 100° C. overnight. After work-up 1.2 g of solid product was obtained. LC/MS: 387.1 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07776874B2
Source datasetuspto-grants-2010_08
ORD IDord-39955b1ef10f4c40a1f382ac516f570e
Source noteuspto-grants-2010_08