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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1485027Generated: October 31, 2026

Citric Acid → 1-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl ester

https://huagongshe.com/reaction/1485027

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCitric AcidHCID 311—
ReactantPhenolHCID 996—
ReactantPotassium CarbonateHCID 11430—
ReactantEthyl 5-Bromo-1-methyl-1H-pyrazole-4-carboxylateHCID 53302113—
SolventDimethylacetamideHCID 31374—
Product1-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl esterHCID 86718550—

Reaction Conditions

Temperature140 °C

Reaction Steps

Phenol (30.29 g; 321.80 mmol) was dissolved in DMA and K2CO3 (88.95 g; 643.60 mmol) was added portion wise. It was stirred for 10 minutes, then 5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (50.0 g; 214.53 mmol) was dropped to the reaction mixture and heated up to 140° C. for 16 hours. A 10% citric acid solution was added and extracted with DCM. The organic layer was washed with sodium bicarbonate and brine, then dried and purified through column chromatography.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09422290B2
Source datasetuspto-grants-2016_08
ORD IDord-70b426cd3fd9498b96b03a79c9a057ce
Source noteuspto-grants-2016_08