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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1693853Generated: October 25, 2026

Acetic Acid → 4-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

https://huagongshe.com/reaction/1693853

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantNitromethaneHCID 6375—
ReactantAmmonium AcetateHCID 517165—
Reactant4-(4-Methyl-pyridin-2-yloxymethyl)-benzaldehydeHCID 59255467—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product4-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridineHCID 59255134109.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

To an acetic acid (20.0 mL) solution of 4-(4-methyl-pyridin-2-yloxymethyl)-benzaldehyde (2.60 g, 11.5 mmol) described in Manufacturing Example 43-1-2 were added nitromethane (3.50 g, 57.3 mmol) and ammonium acetate (1.76 g, 22.9 mmol) at room temperature under nitrogen atmosphere, which was stirred for 4 hours at 100° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.40 g) as a crude product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158657B2
Source datasetuspto-grants-2012_04
ORD IDord-6dd655ea42b64809b66ff904801fa285
Source noteuspto-grants-2012_04