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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 75974Generated: October 28, 2026

Nitrogen → HCID 86666550, compound

https://huagongshe.com/reaction/75974

Reaction equation

Participants

RoleNameHCIDCharge
ReactantNitrogenHCID 947—
ReactantPotassium CarbonateHCID 11430—
Reactant4-FluorobenzaldehydeHCID 68023—
ReactantMethyl 3-(benzyloxy)-5-hydroxybenzoateHCID 7472028—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 86666550HCID 8666655096.5%

Reaction Conditions

Temperature90 °C

Reaction Steps

To a single necked round bottomed flask fitted with stop cock with N2(g) balloon, in DMF was added Methyl 3-(benzyloxy)-5-hydroxybenzoate (24 g) (Intermediate 12). Under stirring, potassium carbonate (38 g) followed by 4-fluorobenzaldehyde (13.84 g) were added at room temperature. The reaction was heated at 90° C. for 16 h with constant stirring. The reaction mixture was diluted with water and extracted with EtOAc. All organic layers were combined and washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to get crude thick liquid product. The crude product was purified by flash column chromatography to yield title compound (32.5 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835469B2
Source datasetuspto-grants-2014_09
ORD IDord-67941696561f4572973b640745d35d6a
Source noteuspto-grants-2014_09