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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 278979Generated: October 27, 2026

Formaldehyde → 8H-5,9,11-trioxabenzo[de]anthracene-4,6-dione

https://huagongshe.com/reaction/278979

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
ReactantSulfuric AcidHCID 1118—
Reactant1,4-DioxaneHCID 31275—
Reactant4-Hydroxy-1,8-naphthalenedicarboxylic anhydrideHCID 5999497—
Product8H-5,9,11-trioxabenzo[de]anthracene-4,6-dioneHCID 22623907—

Reaction Steps

To a suspension of 620 mg (2.9 mmol) of 4-hydroxy-1,8-naphthalic anhydride (from Example S3) and 1.60 g (53.0 mmol) of paraformaldehyde in 20 mL dioxane was added 5.2 mL of concentrated sulfuric acid. The reaction mixture was refluxed for 1 hour and quenched with 100 mL water. The precipitate was isolated, dried, recrystallized from DMSO, washed with acetone, and dried again to yield 0.50 g of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06362181B1
Source datasetuspto-grants-2002_03
ORD IDord-4ada7a95619746e099c34d5eaba90223
Source noteuspto-grants-2002_03