3,4,5-Trimethoxybenzaldehyde → HCID 54489925, compound

HRID 1030199Notes

Reaction equation

[C:1]([O:10]CC)(=[O:9])[CH2:2][CH2:3][C:4]([O:6]CC)=[O:5].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[CH:18]=O.[H-].[Na+].[OH-].[Na+]>C(O)C>[CH3:26][O:25][C:21]1[CH:20]=[C:17]([CH:18]=[C:3]([CH2:2][C:1]([OH:10])=[O:9])[C:4]([OH:6])=[O:5])[CH:16]=[C:15]([O:14][CH3:13])[C:22]=1[O:23][CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred mixture of 17.4 g of diethyl succinate, 19.6 g of 3,4,5-trimethoxybenzaldehyde in 175 ml of ethanol chilled to 0° C. under argon was added 5.0 g of sodium hydride (60% in oil) in three equal portions. The solution was then refluxed for 30 minutes and 125 ml of 2N sodium hydroxide added. The solution was refluxed for 2 hours and concentrated under vacuum. The residue was diluted with water, extracted with ether and the aqueous layer acidified with concentrated hydrochloric acid. The mixture was extracted three times with 45 ml of ether and the ether extracts washed with saturated sodium chloride solution. The ether layer was dried (MgSO4) and the solvent removed under vacuum to give 24.82 g of [(3,4,5-trimethoxyphenyl)methylene]butanedioic acid as a yellow oil.

Workup

temperatureThe solution was then refluxed for 30 minutes
temperatureThe solution was refluxed for 2 hours
concentrationconcentrated under vacuum
additionThe residue was diluted with water
extractionextracted with ether
extractionThe mixture was extracted three times with 45 ml of ether
washthe ether extracts washed with saturated sodium chloride solution
dry with materialThe ether layer was dried (MgSO4)
customthe solvent removed under vacuum

Sources & evidence

ORD record: ord-be4343a0d19243bf95f1135056fe698a
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104869

Reaction notes

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