4-Methoxyphenylacetic Acid → 1-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanone
Reaction equation
[Na].C[Si](C)(C)N[Si](C)(C)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][CH:14]=1.[Cl:23][C:24]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:25]=1C(OC)=O>C1COCC1>[Cl:23][C:24]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:25]=1[C:20](=[O:22])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=1Participants
Procedure
413 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to −65° C., under a nitrogen atmosphere, 300 ml of THF are added, followed dropwise by a solution of 55 g of 4-methoxyphenylacetic acid in 70 ml of THF and the mixture is kept stirred for 3 hours at a temperature of less than −45° C. 64.5 g of methyl 2,4-dichlorobenzoate are then added dropwise and the mixture is kept stirred while the temperature is allowed to rise to 0° C. The reaction mixture is poured over an ice/1 liter 2N HCl mixture, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluted with heptane and then with the heptane/AcOEt mixture to (90/10; v/v). 29 g of the expected compound are obtained.
Workup
- stirringthe mixture is kept stirred while the temperature
- customto rise to 0° C
- extractionextracted with ether
- washthe organic phase is washed with a saturated NaHCO3 solution
- dry with materialdried over Na2SO4
- customthe solvent is evaporated under vacuum
- customThe residue is chromatographed on silica gel
- washeluted with heptane
Sources & evidence
- ORD record
- ord-84530adec181439a8861cbe231ad7f9f
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687537B2
Reaction notes
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