Water → Methyl 3-[2,4-dimethoxy-5-(4-methoxybenzoyl)phenyl]propionate

HRID 893417Notes

Reaction equation

[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=1[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].O>ClCCCl.C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([C:11](=[O:12])[C:10]2[CH:14]=[CH:15][C:7]([O:6][CH3:5])=[CH:8][CH:9]=2)=[CH:20][C:19]=1[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

36.6 g of aluminum trichloride are suspended in 130 ml of 1,2-dichloroethane, and 42.65 g of 4-methoxybenzoyl chloride are added to the mixture which has been cooled to 0° C. Then, at this temperature, 56 g of methyl 3-(2,4-dimethoxyphenyl)propionate (Example 17) dissolved in 30 ml of 1,2-dichloroethane are added dropwise, and the mixture is then stirred at 50° C. with exclusion of moisture until the reaction is complete (about 36 hours). 200 ml of water are added to the cooled reaction mixture which is then diluted with 400 ml of CH2Cl2, extracted with bicarbonate and water, dried over sodium sulfate and concentrated. The residue is dissolved in diisopropyl ether and precipitated with hexane. Filtration with suction results in 62.1 g of the product, and a further 10.5 g from the mother liquor.

Workup

additionare added dropwise
custom(about 36 hours)
extractionextracted with bicarbonate and water
dry with materialdried over sodium sulfate
concentrationconcentrated
dissolutionThe residue is dissolved in diisopropyl ether
customprecipitated with hexane
filtrationFiltration with suction

Sources & evidence

ORD record: ord-158d414b12874067a340b61104f0f31a
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05124478

Reaction notes

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