Acetic Acid → 3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-4-oxo-4H-chromene-8-carbaldehyde

HRID 14499

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:20]([CH3:22])[CH3:21])=[CH:4][CH:3]=1.C1N2CN3CN(C2)CN1C3.Cl.[C:34](O)(=[O:36])C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH:34]=[O:36])[C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:20]([CH3:22])[CH3:21])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-chromen-4-one (12.48 g, 39.6 mmol) and hexamethylenetetramine (39.46 g, 0.28 mol) in acetic acid (250 ml) is stirred at 100° C. for 20 h. After the mixture has cooled to room temperature, the solvent is removed in vacuo to afford a black oily residue. 5M HCl solution (150 ml) is added, and the mixture is heated under reflux for 30 min. The reaction mixture is poured onto ice/water, and the resulting brown solid is isolated by filtration. The solid is taken up in dichloromethane, the mixture is passed through a bed of Celite, and the solvent is evaporated in vacuo. The solid residue is stirred at room temperature with ethyl acetate, filtered and washed with hexane to afford the desired product as a pale brown solid.

Workup

temperatureAfter the mixture has cooled to room temperature
customthe solvent is removed in vacuo
customto afford a black oily residue
temperaturethe mixture is heated
temperatureunder reflux for 30 min
additionThe reaction mixture is poured onto ice/water
customthe resulting brown solid is isolated by filtration
customthe solvent is evaporated in vacuo
stirringThe solid residue is stirred at room temperature with ethyl acetate
filtrationfiltered
washwashed with hexane

Sources & evidence

ORD record: ord-e03fad2a09ea4f109a4d38cc1e388195
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732435B2

Linked notes

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