Hexamethylenetetramine → 2-oxo-2H-chromene-6-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Hexamethylenetetramine	HCID 4101	—
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	3-Benzyl-4-methylumbelliferone	HCID 5338538	—
Product	2-oxo-2H-chromene-6-carbaldehyde	HCID 2735831	—
Product	2-oxo-2H-chromene-8-carbaldehyde	HCID 22218393	—

Reaction Steps

2-Oxo-3-benzyl-4-methyl-7-hydroxyl-2H-1-benzopyrane (512 mg, Example 1) and HMTA (140 mg) are mixed in TFA (5 mL). The reaction mixture is heated at reflux overnight. The solvent is removed under reduced pressure. The residue is purified over silica gel column (Hexanes:EtOAc, 85:15) to afford the desired 8-formyl coumarin (107 mg) and 6-formyl coumarin derivative (35 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07994318B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-5e1d25aa90b14e26a8e3de6e59eb7850
Source note	uspto-grants-2011_08