Formaldehyde → HCID 211864, compound

HRID 1629970Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].[CH2:14]=O.Cl.[CH3:17][NH:18][CH3:19]>C(O)C>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH2:1][CH2:17][N:18]([CH3:14])[CH3:19])[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 3,4-Dimethoxy acetophenone (3 g, 0.0166 moles, 1 equiv.) in ethanol was added paraformaldehyde (0.5 g, 0.0166 moles, 1 equiv.), dimethylamine hydrochloride (4.2 g, 0.0499 moles, 3 equiv.) and the reaction mixture was refluxed at 80° C. for 12 h. Consumption of starting materials was confirmed by LC-MS analysis and TLC. Ethanol was evaporated under reduced pressure; the crude solid residue was stirred with acetone at 0° C. for 1 h, filtered, washed with acetone, dried under vacuum. After that the solid was suspended in water, basified with 10% sodium bicarbonate solution (pH˜8), extracted by dichloromethane (2×200 ml), washed with water followed by satd. Brine solution. The organic layer was dried over sodium sulfate and concentrated to get 2.9 g (73% yield) title compound as green oily liquid. It was taken forward for the next step without any further purification.

Workup

customConsumption of starting materials
customEthanol was evaporated under reduced pressure
filtrationfiltered
washwashed with acetone
customdried under vacuum
extractionextracted by dichloromethane (2×200 ml)
washwashed with water
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-31f0523e151347f4a1ccf4d0ceccd9a8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791114B2

Reaction notes

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