Methane, dichloromethoxy- → 2-(3-methyl-2-Formyl-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

HRID 1692618Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([O:23][CH3:24])[CH:17]=1.[CH3:26][O:27]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[O:15][C:16]1[CH:17]=[C:18]([O:23][CH3:24])[CH:19]=[C:20]([CH3:22])[C:21]=1[CH:26]=[O:27]

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 1 mmol of 3,5-dimethoxy-2-(5-methyl-3-methoxy-phenoxy)-4-methyl-benzoic acid methyl ester and 6 mmol of dichloromethyl methyl ether was taken in 8 mL of dichloromethane. The mixture was cooled to −78° C. under stirring, and then titanium tetrachloride (6 mmol) in dichloromethane (4 ml) was added dropwise over 0.5 h. Upon completion, the reaction mixture was poured into ice-cold water and partitioned. The layers were separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over MgSO4, and the solvent was evaporated by a rotary evaporator. The residue was purified by column chromatography to afford 2-(3-methyl-2-Formyl-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (60%).

Workup

additionUpon completion, the reaction mixture was poured into ice-cold water
custompartitioned
customThe layers were separated
extractionthe aqueous layer was extracted with dichloromethane
dry with materialThe combined organic layers were dried over MgSO4
customthe solvent was evaporated by a rotary evaporator
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-511691820b144b2cbc1c15bf6e404718
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158623B2

Reaction notes

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