Dimethylformamide → HCID 18383995, compound

HRID 2297731Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].[C:12](=[O:15])([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20]Cl.[CH3:22]N(C)C=O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:22][O:15][CH3:12])[C:9]=1[O:10][CH2:18][O:19][CH3:20])[CH:5]=[O:6]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7864Chloromethyl Methyl Ether

HCID 11430Potassium Carbonate

HCID 836513,4,5-Trihydroxybenzaldehyde

Product 1

HCID 18383995HCID 18383995, compoundYield 17%

Procedure

3,4,5-Trihydroxybenzaldehyde (628 mg, 3.6 mmol) was dissolved in dimethylformamide (30 mL), and potassium carbonate (2.0 g, 14 mmol) was added thereto, followed by stirring at room temperature for 30 minutes. Next, chloromethyl methyl ether (0.96 mL, 13 mmol) was added thereto, followed by stirring at room temperature for 2 hours. After the conventional post-treatment, the residue was purified by preparative thin layer chromatography (developed with chloroform/methanol=98/2) to give 3-hydroxy-4,5-bis(methoxymethoxy)benzaldehyde (140 mg, yield 17%).

Workup

stirringby stirring at room temperature for 2 hours
customAfter the conventional post-treatment, the residue was purified by preparative thin layer chromatography (developed with chloroform/methanol=98/2)

Sources & evidence

ORD record: ord-21707e02c84548ddb23ab068bf97fe96
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492392B1

Reaction notes

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